Rdkit-based data preparation

Author
Affiliation

Paweł Wiczling*

Department of Biopharmaceutics and Pharmacodynamics, Medical University of Gdańsk, Gen. J. Hallera 107, 80-416 Gdańsk, Poland

Published

May 8, 2025

Introductions

…

Setup

Code 
library(ggplot2)
library(gridExtra)
library(patchwork)
library(tidyr)
library(dplyr)
library(GGally)
library(reshape2)
library(pracma)
library(here)
library(magick)
library(reticulate)
library(kableExtra)
require(visNetwork, quietly = TRUE)
library(igraph)
library(ggraph)
#remotes::install_github("metrumresearchgroup/mrgmisc")
library(tidyverse)
library(patchwork)

set.seed(10271998) ## not required but assures repeatable results

source("helper-functions.R")
Code 
data_deliv_dir = here::here("data","deliv")
data_derived_dir = here::here("data","derived")
if(!file.exists(data_deliv_dir)) dir.create(data_deliv_dir, recursive = T)
if(!file.exists(data_derived_dir)) dir.create(data_derived_dir, recursive = T)

figures_eda_dir <- here::here("deliv","figures", "eda")
tables_eda_dir <- here::here("deliv","tables", "eda")
if(!file.exists(figures_eda_dir)) dir.create(figures_eda_dir, recursive = T)
if(!file.exists(tables_eda_dir)) dir.create(tables_eda_dir, recursive = T)

model_dir <- here::here("model","stan")  
figures_dir <- here::here("deliv","figures", "stan")
tables_dir <- here::here("deliv","tables", "stan")
if(!file.exists(figures_dir)) dir.create(figures_dir, recursive = T)
if(!file.exists(model_dir)) dir.create(model_dir, recursive = T)
if(!file.exists(tables_dir)) dir.create(tables_dir, recursive = T)

Load data

Code 
data <- read.csv(here(data_deliv_dir, "database_logk_1026.csv"), header = TRUE)
analytes_names  <- read.csv(here(data_deliv_dir,"database_logk_1026_analyte_names.csv"), header = TRUE)
smiles <- read.csv(here(data_deliv_dir,"smiles1026.smi"), sep = "\t", header = FALSE)
functional_groups = read.csv(here(data_deliv_dir, 'checkmol_functional_groups.csv'))
functional_groups_names = read.csv(here(data_deliv_dir,'checkmol_functional_group_names.csv'))
data_ACD = read.csv(here(data_deliv_dir,'ACD_pKas.csv'))
data_pH <- read.csv(here(data_deliv_dir,"pH.csv"),header = TRUE)

results = read.csv(file = here(data_deliv_dir,"results_table_max_frag_size.csv"), header = TRUE)
comparison_table = read.csv(file = here(data_deliv_dir,"comparison_table.csv"), header = TRUE)
comparison_table_add = read.csv(file = here(data_deliv_dir,"comparison_table_add.csv"), header = TRUE)
comparison_table_remove = read.csv(file = here(data_deliv_dir,"comparison_table_remove.csv"), header = TRUE)

fg_df = read.csv(file = here(data_deliv_dir,"smarts_functional_groups.csv"), header = TRUE)
fg_df_common1 = read.csv(file = here(data_deliv_dir,"smarts_functional_groups_common1.csv"), header = TRUE)
fg_df_common2 = read.csv(file = here(data_deliv_dir,"smarts_functional_groups_common2.csv"), header = TRUE)

smiles<-smiles %>% rename(ID=V2,smiles=V1) %>% select(ID,smiles)
smiles$smiles[905] = "CN(C1CCCCC1N1CCCC1)C(=O)Cc1ccc(c(c1)Cl)Cl" # remove tartrate moiety 
smiles$smiles[425] = "CC(Cc1ccc(cc1)OCC(=O)O)NCC(c1cccc(c1)Cl)O" # remove Na+ and dissociation
smiles$smiles[501] = "c1ccc(cc1)C1(c2ccccc2)C(=O)NC(=N1)O"
smiles$smiles[401]= "CC(C)(C)c1c(CC(C(=O)[OH])[NH2])c(=O)[nH]o1"
smiles$smiles[686] = "CCCCCCCCCCCCCCCC(=O)OC(CC(=O)[OH])C[N+](C)(C)C"
smiles$smiles[901] = "CCOC(=Nc1c[n+](no1)N1CCOCC1)[OH]"

analytes_names$Analyte <- iconv(analytes_names$Analyte, from = "", to = "UTF-8", sub = "byte")

Python

Code 
# use_condaenv("rdkit-env", conda = "C:/Users/GUMed/anaconda3/Scripts/conda.exe", required = TRUE)
#.Renviron
Code 
Chem <- import("rdkit.Chem")
AllChem <- import("rdkit.Chem.AllChem")
Draw <- import("rdkit.Chem.Draw")
rdFMCS <- import("rdkit.Chem.rdFMCS")
rdmolops <- import("rdkit.Chem.rdmolops")
FunctionalGroups <- Chem$FunctionalGroups

# Create MCS parameters
mcs_params <- rdFMCS$MCSParameters()
mcs_params$AtomCompareParameters$MatchValences <- TRUE
mcs_params$AtomCompareParameters$RingMatchesRingOnly <- TRUE
mcs_params$AtomCompareParameters$CompleteRingsOnly <- TRUE
mcs_params$AtomCompare <- rdFMCS$AtomCompare$CompareElements
mcs_params$BondCompare <- rdFMCS$BondCompare$CompareOrderExact
mcs_params$BondCompareParameters$CompleteRingsOnly <- TRUE
mcs_params$BondCompareParameters$RingMatchesRingOnly <- TRUE
mcs_params$Timeout <- 20L
mcs_params$Verbose <- FALSE
mcs_params$Threshold <- 1.0
mcs_params$MaximizeBonds<-TRUE

custom_groups <- list(
  list(name = "Primary_carbon", smarts = "[CX4H3][#6]"),
  list(name = "Secondary_carbon", smarts = "[CX4H2]([#6])[#6]"),
  list(name = "Tertiary_carbon", smarts = "[CX4H1]([#6])([#6])[#6]"),
  list(name = "Quaternary_carbon", smarts = "[CX4H0]([#6])([#6])([#6])[#6]"),
  list(name = "Alkene", smarts = "[CX3;$([H2]),$([H1][#6]),$(C([#6])[#6])]=[CX3;$([H2]),$([H1][#6]),$(C([#6])[#6])]"),
  list(name = "Alkyne", smarts = "[CX2]#[CX2]"),
  list(name = "Allene", smarts = "[CX3]=[CX2]=[CX3]"),
  list(name = "Alkylchloride", smarts = "[ClX1][CX4]"),
  list(name = "Alkylfluoride", smarts = "[FX1][CX4]"),
  list(name = "Alkylbromide", smarts = "[BrX1][CX4]"),
  list(name = "Alkyliodide", smarts = "[IX1][CX4]"),
  list(name = "Primary_alcohol", smarts = "[OX2H][CX4H2;!$(C([OX2H])[O,S,#7,#15])]"),
  list(name = "Secondary_alcohol", smarts = "[OX2H][CX4H;!$(C([OX2H])[O,S,#7,#15])]"),
  list(name = "Tertiary_alcohol", smarts = "[OX2H][CX4D4;!$(C([OX2H])[O,S,#7,#15])]"),
  list(name = "Dialkylether", smarts = "[OX2]([CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([OX2])[O,S,#7,#15])]"),
  list(name = "Dialkylthioether", smarts = "[SX2]([CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([OX2])[O,S,#7,#15])]"),
  list(name = "Alkylarylether", smarts = "[OX2](c)[CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])]"),
  list(name = "Diarylether", smarts = "[c][OX2][c]"),
  list(name = "Alkylarylthioether", smarts = "[SX2](c)[CX4;!$(C([OX2])[O,S,#7,#15,F,Cl,Br,I])]"),
  list(name = "Diarylthioether", smarts = "[c][SX2][c]"),
  list(name = "Oxonium", smarts = "[O+;!$([O]~[!#6]);!$([S]*~[#7,#8,#15,#16])]"),
  list(name = "Primary_aliph_amine", smarts = "[NX3H2+0,NX4H3+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Secondary_aliph_amine", smarts = "[NX3H1+0,NX4H2+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Tertiary_aliph_amine", smarts = "[NX3H0+0,NX4H1+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Quaternary_aliph_ammonium", smarts = "[NX4H0+;!$([N][!C]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Primary_arom_amine", smarts = "[NX3H2+0,NX4H3+]c"),
  list(name = "Secondary_arom_amine", smarts = "[NX3H1+0,NX4H2+;!$([N][!c]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Tertiary_arom_amine", smarts = "[NX3H0+0,NX4H1+;!$([N][!c]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Quaternary_arom_ammonium", smarts = "[NX4H0+;!$([N][!c]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Secondary_mixed_amine", smarts = "[NX3H1+0,NX4H2+;$([N]([c])[C]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Tertiary_mixed_amine", smarts = "[NX3H0+0,NX4H1+;$([N]([c])([C])[#6]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Quaternary_mixed_ammonium", smarts = "[NX4H0+;$([N]([c])([C])[#6][#6]);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Ammonium", smarts = "[N+;!$([N]~[!#6]);!$(N=*);!$([N]*~[#7,#8,#15,#16])]"),
  list(name = "Alkylthiol", smarts = "[SX2H][CX4;!$(C([SX2H])~[O,S,#7,#15])]"),
  #list(name = "Dialkylthioether", smarts = "[SX2]([CX4;!$(C([SX2])[O,S,#7,#15,F,Cl,Br,I])])[CX4;!$(C([SX2])[O,S,#7,#15])]"),
  #list(name = "Alkylarylthioether", smarts = "[SX2](c)[CX4;!$(C([SX2])[O,S,#7,#15])]"),
  list(name = "Disulfide", smarts = "[SX2D2][SX2D2]"),
  list(name = "1,2-Aminoalcohol", smarts = "[OX2H][CX4;!$(C([OX2H])[O,S,#7,#15,F,Cl,Br,I])][CX4;!$(C([N])[O,S,#7,#15])][NX3;!$(NC=[O,S,N])]"),
  list(name = "1,2-Diol", smarts = "[OX2H][CX4;!$(C([OX2H])[O,S,#7,#15])][CX4;!$(C([OX2H])[O,S,#7,#15])][OX2H]"),
  list(name = "1,1-Diol", smarts = "[OX2H][CX4;!$(C([OX2H])([OX2H])[O,S,#7,#15])][OX2H]"),
  list(name = "Hydroperoxide", smarts = "[OX2H][OX2]"),
  list(name = "Peroxo", smarts = "[OX2D2][OX2D2]"),
  list(name = "Organolithium_compounds", smarts = "[LiX1][#6,#14]"),
  list(name = "Organomagnesium_compounds", smarts = "[MgX2][#6,#14]"),
  list(name = "Organometallic_compounds", smarts = "[!#1;!#5;!#6;!#7;!#8;!#9;!#14;!#15;!#16;!#17;!#33;!#34;!#35;!#52;!#53;!#85]~[#6;!-]"),
  list(name = "Aldehyde", smarts = "[$([CX3H][#6]),$([CX3H2])]=[OX1]"),
  list(name = "Ketone", smarts = "[#6][CX3](=[OX1])[#6]"),
  list(name = "Thioaldehyde", smarts = "[$([CX3H][#6]),$([CX3H2])]=[SX1]"),
  list(name = "Thioketone", smarts = "[#6][CX3](=[SX1])[#6]"),
  list(name = "Imine", smarts = "[NX2;$([N][#6]),$([NH]);!$([N][CX3]=[#7,#8,#15,#16])]=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])]"),
  list(name = "Immonium", smarts = "[NX3+;!$([N][!#6]);!$([N][CX3]=[#7,#8,#15,#16])]"),
  list(name = "Oxime", smarts = "[NX2](=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])])[OX2H]"),
  list(name = "Oximether", smarts = "[NX2](=[CX3;$([CH2]),$([CH][#6]),$([C]([#6])[#6])])[OX2][#6;!$(C=[#7,#8])]"),
  list(name = "Acetal", smarts = "[OX2]([#6;!$(C=[O,S,N])])[CX4;!$(C(O)(O)[!#6])][OX2][#6;!$(C=[O,S,N])]"),
  list(name = "Hemiacetal", smarts = "[OX2H][CX4;!$(C(O)(O)[!#6])][OX2][#6;!$(C=[O,S,N])]"),
  list(name = "Aminal", smarts = "[NX3v3;!$(NC=[#7,#8,#15,#16])]([#6])[CX4;!$(C(N)(N)[!#6])][NX3v3;!$(NC=[#7,#8,#15,#16])][#6]"),
  list(name = "Hemiaminal", smarts = "[NX3v3;!$(NC=[#7,#8,#15,#16])]([#6])[CX4;!$(C(N)(N)[!#6])][OX2H]"),
  list(name = "Thioacetal", smarts = "[SX2]([#6;!$(C=[O,S,N])])[CX4;!$(C(S)(S)[!#6])][SX2][#6;!$(C=[O,S,N])]"),
  list(name = "Thiohemiacetal", smarts = "[SX2]([#6;!$(C=[O,S,N])])[CX4;!$(C(S)(S)[!#6])][OX2H]"),
  list(name = "Halogen_acetal_like", smarts = "[NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1]"),
  list(name = "Acetal_like", smarts = "[NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1,NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])]"),
  list(name = "Halogenmethylen_ester_and_similar", smarts = "[NX3v3,SX2,OX2;$(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1]"),
  list(name = "NOS_methylen_ester_and_similar", smarts = "[NX3v3,SX2,OX2;$(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])]"),
  list(name = "Hetero_methylen_ester_and_similar", smarts = "[NX3v3,SX2,OX2;$(**=[#7,#8,#15,#16])][CX4;!$(C([N,S,O])([N,S,O])[!#6])][FX1,ClX1,BrX1,IX1,NX3v3,SX2,OX2;!$(*C=[#7,#8,#15,#16])]"),
  list(name = "Cyanhydrine", smarts = "[NX1]#[CX2][CX4;$([CH2]),$([CH]([CX2])[#6]),$(C([CX2])([#6])[#6])][OX2H]"),
  list(name = "Chloroalkene", smarts = "[ClX1][CX3]=[CX3]"),
  list(name = "Fluoroalkene", smarts = "[FX1][CX3]=[CX3]"),
  list(name = "Bromoalkene", smarts = "[BrX1][CX3]=[CX3]"),
  list(name = "Iodoalkene", smarts = "[IX1][CX3]=[CX3]"),
  list(name = "Enol", smarts = "[OX2H][CX3;$([H1]),$(C[#6])]=[CX3]"),
  list(name = "Endiol", smarts = "[OX2H][CX3;$([H1]),$(C[#6])]=[CX3;$([H1]),$(C[#6])][OX2H]"),
  list(name = "Enolether", smarts = "[OX2]([#6;!$(C=[N,O,S])])[CX3;$([H0][#6]),$([H1])]=[CX3]"),
  list(name = "Enolester", smarts = "[OX2]([CX3]=[OX1])[#6X3;$([#6][#6]),$([H1])]=[#6X3;!$(C[OX2H])]"),
  list(name = "Enamine", smarts = "[NX3;$([NH2][CX3]),$([NH1]([CX3])[#6]),$([N]([CX3])([#6])[#6]);!$([N]*=[#7,#8,#15,#16])][CX3;$([CH]),$([C][#6])]=[CX3]"),
  list(name = "Thioenol", smarts = "[SX2H][CX3;$([H1]),$(C[#6])]=[CX3]"),
  list(name = "Thioenolether", smarts = "[SX2]([#6;!$(C=[N,O,S])])[CX3;$(C[#6]),$([CH])]=[CX3]"),
  list(name = "Acylchloride", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[ClX1]"),
  list(name = "Acylfluoride", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[FX1]"),
  list(name = "Acylbromide", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[BrX1]"),
  list(name = "Acyliodide", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[IX1]"),
  list(name = "Carboxylic_acid", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[$([OX2H]),$([OX1-])]"),
  list(name = "Carboxylic_ester", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Lactone", smarts = "[#6][#6X3R](=[OX1])[#8X2][#6;!$(C=[O,N,S])]"),
  list(name = "Carboxylic_anhydride", smarts = "[CX3;$([H0][#6]),$([H1])](=[OX1])[#8X2][CX3;$([H0][#6]),$([H1])](=[OX1])"),
  list(name = "Carbothioic_acid", smarts = "[CX3;!R;$([C][#6]),$([CH]);$([C](=[OX1])[$([SX2H]),$([SX1-])]),$([C](=[SX1])[$([OX2H]),$([OX1-])])]"),
  list(name = "Carbothioic_S_ester", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[SX2][#6;!$(C=[O,N,S])]"),
  list(name = "Carbothioic_S_lactone", smarts = "[#6][#6X3R](=[OX1])[#16X2][#6;!$(C=[O,N,S])]"),
  list(name = "Carbothioic_O_ester", smarts = "[CX3;$([H0][#6]),$([H1])](=[SX1])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Carbothioic_O_lactone", smarts = "[#6][#6X3R](=[SX1])[#8X2][#6;!$(C=[O,N,S])]"),
  list(name = "Carbothioic_halide", smarts = "[CX3;$([H0][#6]),$([H1])](=[SX1])[FX1,ClX1,BrX1,IX1]"),
  list(name = "Carbodithioic_acid", smarts = "[CX3;!R;$([C][#6]),$([CH]);$([C](=[SX1])[SX2H])]"),
  list(name = "Carbodithioic_ester", smarts = "[CX3;!R;$([C][#6]),$([CH]);$([C](=[SX1])[SX2][#6;!$(C=[O,N,S])])]"),
  list(name = "Carbodithiolactone", smarts = "[#6][#6X3R](=[SX1])[#16X2][#6;!$(C=[O,N,S])]"),
  list(name = "Primary_amide", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[NX3H2]"),
  list(name = "Secondary_amide", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[#7X3H1][#6;!$(C=[O,N,S])]"),
  list(name = "Tertiary_amide", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[#7X3H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])]"),
  list(name = "Lactam", smarts = "[#6R][#6X3R](=[OX1])[#7X3;$([H1][#6;!$(C=[O,N,S])]),$([H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Alkyl_imide", smarts = "[#6X3;$([H0][#6]),$([H1])](=[OX1])[#7X3H0]([#6])[#6X3;$([H0][#6]),$([H1])](=[OX1])"),
  list(name = "N_hetero_imide", smarts = "[#6X3;$([H0][#6]),$([H1])](=[OX1])[#7X3H0]([!#6])[#6X3;$([H0][#6]),$([H1])](=[OX1])"),
  list(name = "Imide_acidic", smarts = "[#6X3;$([H0][#6]),$([H1])](=[OX1])[#7X3H1][#6X3;$([H0][#6]),$([H1])](=[OX1])"),
  list(name = "Thioamide", smarts = "[$([CX3;!R][#6]),$([CX3H;!R])](=[SX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Thiolactam", smarts = "[#6R][#6X3R](=[SX1])[#7X3;$([H1][#6;!$(C=[O,N,S])]),$([H0]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Oxim ester", smarts = "[#6X3;$([H0][#6]),$([H1])](=[OX1])[#8X2][#7X2]=,:[#6X3;$([H0]([#6])[#6]),$([H1][#6]),$([H2])]"),
  list(name = "Amidine", smarts = "[NX3;!$(NC=[O,S])][CX3;$([CH]),$([C][#6])]=[NX2;!$(NC=[O,S])]"),
  list(name = "Hydroxamic_acid", smarts = "[CX3;$([H0][#6]),$([H1])](=[OX1])[#7X3;$([H1]),$([H0][#6;!$(C=[O,N,S])])][$([OX2H]),$([OX1-])]"),
  list(name = "Hydroxamic_acid_ester", smarts = "[CX3;$([H0][#6]),$([H1])](=[OX1])[#7X3;$([H1]),$([H0][#6;!$(C=[O,N,S])])][OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Imidoacid", smarts = "[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]"),
  list(name = "Imidoacid_cyclic", smarts = "[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]"),
  list(name = "Imidoester", smarts = "[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Imidolactone", smarts = "[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Imidothioacid", smarts = "[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([SX2H]),$([SX1-])]"),
  list(name = "Imidothioacid_cyclic", smarts = "[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[$([SX2H]),$([SX1-])]"),
  list(name = "Imidothioester", smarts = "[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[SX2][#6;!$(C=[O,N,S])]"),
  list(name = "Imidothiolactone", smarts = "[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[SX2][#6;!$(C=[O,N,S])]"),
  list(name = "Imidolactam", smarts = "[#6][#6X3R;$([H0](=[NX2;!$(N(=[#6X3][#7X3])C=[O,S])])[#7X3;!$(N([#6X3]=[#7X2])C=[O,S])]),$([H0](-[NX3;!$(N([#6X3]=[#7X2])C=[O,S])])=,:[#7X2;!$(N(=[#6X3][#7X3])C=[O,S])])]"),
  list(name = "Imidoylhalide", smarts = "[CX3R0;$([H0][#6]),$([H1])](=[NX2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[FX1,ClX1,BrX1,IX1]"),
  list(name = "Imidoylhalide_cyclic", smarts = "[#6R][#6X3R](=,:[#7X2;$([H1]),$([H0][#6;!$(C=[O,N,S])])])[FX1,ClX1,BrX1,IX1]"),
  list(name = "Amidrazone", smarts = "[$([$([#6X3][#6]),$([#6X3H])](=[#7X2v3])[#7X3v3][#7X3v3]),$([$([#6X3][#6]),$([#6X3H])]([#7X3v3])=[#7X2v3][#7X3v3])]"),
  list(name = "Alpha_aminoacid", smarts = "[NX3,NX4+;!$([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])][C][CX3](=[OX1])[OX2H,OX1-]"),
  list(name = "Alpha_hydroxyacid", smarts = "[OX2H][C][CX3](=[OX1])[OX2H,OX1-]"),
  list(name = "Peptide_middle", smarts = "[NX3;$([N][CX3](=[OX1])[C][NX3,NX4+])][C][CX3](=[OX1])[NX3;$([N][C][CX3](=[OX1])[NX3,OX2,OX1-])]"),
  list(name = "Peptide_C_term", smarts = "[NX3;$([N][CX3](=[OX1])[C][NX3,NX4+])][C][CX3](=[OX1])[OX2H,OX1-]"),
  list(name = "Peptide_N_term", smarts = "[NX3,NX4+;!$([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])][C][CX3](=[OX1])[NX3;$([N][C][CX3](=[OX1])[NX3,OX2,OX1-])]"),
  list(name = "Carboxylic_orthoester", smarts = "[#6][OX2][CX4;$(C[#6]),$([CH])]([OX2][#6])[OX2][#6]"),
  list(name = "Ketene", smarts = "[CX3]=[CX2]=[OX1]"),
  list(name = "Ketenacetal", smarts = "[#7X2,#8X3,#16X2;$(*[#6,#14])][#6X3]([#7X2,#8X3,#16X2;$(*[#6,#14])])=[#6X3]"),
  list(name = "Nitrile", smarts = "[NX1]#[CX2]"),
  list(name = "Isonitrile", smarts = "[CX1-]#[NX2+]"),

  list(name = "Carbonic_acid_dieester", smarts = "[#6;!$(C=[O,N,S])][#8X2][#6X3](=[OX1])[#8X2][#6;!$(C=[O,N,S])]"),
  list(name = "Carbonic_acid_esterhalide", smarts = "[#6;!$(C=[O,N,S])][OX2;!R][CX3](=[OX1])[OX2][FX1,ClX1,BrX1,IX1]"),
  list(name = "Carbonic_acid_monoester", smarts = "[#6;!$(C=[O,N,S])][OX2;!R][CX3](=[OX1])[$([OX2H]),$([OX1-])]"),
  list(name = "Thiocarbonic_acid_dieester", smarts = "[#6;!$(C=[O,N,S])][#8X2][#6X3](=[SX1])[#8X2][#6;!$(C=[O,N,S])]"),
  list(name = "Thiocarbonic_acid_esterhalide", smarts = "[#6;!$(C=[O,N,S])][OX2;!R][CX3](=[SX1])[OX2][FX1,ClX1,BrX1,IX1]"),
  list(name = "Thiocarbonic_acid_monoester", smarts = "[#6;!$(C=[O,N,S])][OX2;!R][CX3](=[SX1])[$([OX2H]),$([OX1-])]"),
  list(name = "Urea", smarts = "[#7X3;!$([#7][!#6])][#6X3](=[OX1])[#7X3;!$([#7][!#6])]"),
  list(name = "Thiourea", smarts = "[#7X3;!$([#7][!#6])][#6X3](=[SX1])[#7X3;!$([#7][!#6])]"),
  list(name = "Isourea", smarts = "[#7X2;!$([#7][!#6])]=,:[#6X3]([#8X2&!$([#8][!#6]),OX1-])[#7X3;!$([#7][!#6])]"),
  list(name = "Isothiourea", smarts = "[#7X2;!$([#7][!#6])]=,:[#6X3]([#16X2&!$([#16][!#6]),SX1-])[#7X3;!$([#7][!#6])]"),
  list(name = "Guanidine", smarts = "[N;v3X3,v4X4+][CX3](=[N;v3X2,v4X3+])[N;v3X3,v4X4+]"),
  list(name = "Carbaminic_acid", smarts = "[NX3]C(=[OX1])[O;X2H,X1-]"),
  list(name = "Urethan", smarts = "[#7X3][#6](=[OX1])[#8X2][#6]"),
  list(name = "Biuret", smarts = "[#7X3][#6](=[OX1])[#7X3][#6](=[OX1])[#7X3]"),
  list(name = "Semicarbazide", smarts = "[#7X3][#7X3][#6X3]([#7X3;!$([#7][#7])])=[OX1]"),
  list(name = "Carbazide", smarts = "[#7X3][#7X3][#6X3]([#7X3][#7X3])=[OX1]"),
  list(name = "Semicarbazone", smarts = "[#7X2](=[#6])[#7X3][#6X3]([#7X3;!$([#7][#7])])=[OX1]"),
  list(name = "Carbazone", smarts = "[#7X2](=[#6])[#7X3][#6X3]([#7X3][#7X3])=[OX1]"),
  list(name = "Thiosemicarbazide", smarts = "[#7X3][#7X3][#6X3]([#7X3;!$([#7][#7])])=[SX1]"),
  list(name = "Thiocarbazide", smarts = "[#7X3][#7X3][#6X3]([#7X3][#7X3])=[SX1]"),
  list(name = "Thiosemicarbazone", smarts = "[#7X2](=[#6])[#7X3][#6X3]([#7X3;!$([#7][#7])])=[SX1]"),
  list(name = "Thiocarbazone", smarts = "[#7X2](=[#6])[#7X3][#6X3]([#7X3][#7X3])=[SX1]"),
  list(name = "Isocyanate", smarts = "[NX2]=[CX2]=[OX1]"),
  list(name = "Cyanate", smarts = "[OX2][CX2]#[NX1]"),
  list(name = "Isothiocyanate", smarts = "[NX2]=[CX2]=[SX1]"),
  list(name = "Thiocyanate", smarts = "[SX2][CX2]#[NX1]"),
  list(name = "Carbodiimide", smarts = "[NX2]=[CX2]=[NX2]"),
  list(name = "Orthocarbonic_derivatives", smarts = "[CX4H0]([O,S,#7])([O,S,#7])([O,S,#7])[O,S,#7,F,Cl,Br,I]"),
  list(name = "Phenol", smarts = "[OX2H][c]"),
  list(name = "1,2-Diphenol", smarts = "[OX2H][c][c][OX2H]"),
  list(name = "Arylchloride", smarts = "[Cl][c]"),
  list(name = "Arylfluoride", smarts = "[F][c]"),
  list(name = "Arylbromide", smarts = "[Br][c]"),
  list(name = "Aryliodide", smarts = "[I][c]"),
  list(name = "Arylthiol", smarts = "[SX2H][c]"),
  list(name = "Iminoarene", smarts = "[c]=[NX2;$([H1]),$([H0][#6;!$([C]=[N,S,O])])]"),
  list(name = "Oxoarene", smarts = "[c]=[OX1]"),
  list(name = "Thioarene", smarts = "[c]=[SX1]"),
  list(name = "Hetero_N_basic_H", smarts = "[nX3H1+0]"),
  list(name = "Hetero_N_basic_no_H", smarts = "[nX3H0+0]"),
  list(name = "Hetero_N_nonbasic", smarts = "[nX2,nX3+]"),
  list(name = "Hetero_O", smarts = "[o]"),
  list(name = "Hetero_S", smarts = "[sX2]"),
  list(name = "Heteroaromatic", smarts = "[a;!c]"),
  list(name = "Nitrite", smarts = "[NX2](=[OX1])[O;$([X2]),$([X1-])]"),
  list(name = "Thionitrite", smarts = "[SX2][NX2]=[OX1]"),
  list(name = "Nitrate", smarts = "[$([NX3](=[OX1])(=[OX1])[O;$([X2]),$([X1-])]),$([NX3+]([OX1-])(=[OX1])[O;$([X2]),$([X1-])])]"),
  list(name = "Nitro", smarts = "[$([NX3](=O)=O),$([NX3+](=O)[O-])][!#8]"),
  list(name = "Nitroso", smarts = "[NX2](=[OX1])[!#7;!#8]"),
  list(name = "Azide", smarts = "[NX1]~[NX2]~[NX2,NX1]"),
  list(name = "Acylazide", smarts = "[CX3](=[OX1])[NX2]~[NX2]~[NX1]"),
  list(name = "Diazo", smarts = "[$([#6]=[NX2+]=[NX1-]),$([#6-]-[NX2+]#[NX1])]"),
  list(name = "Diazonium", smarts = "[#6][NX2+]#[NX1]"),
  list(name = "Nitrosamine", smarts = "[#7;!$(N*=O)][NX2]=[OX1]"),
  list(name = "Nitrosamide", smarts = "[NX2](=[OX1])N-*=O"),
  list(name = "N-Oxide", smarts = "[$([#7+][OX1-]),$([#7v5]=[OX1]);!$([#7](~[O])~[O]);!$([#7]=[#7])]"),
  list(name = "Hydrazine", smarts = "[NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])]"),
  list(name = "Hydrazone", smarts = "[NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][NX2]=[#6]"),
  list(name = "Hydroxylamine", smarts = "[NX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6]);!$(NC=[O,N,S])][OX2;$([H1]),$(O[#6;!$(C=[N,O,S])])]"),
  list(name = "Sulfon", smarts = "[$([SX4](=[OX1])(=[OX1])([#6])[#6]),$([SX4+2]([OX1-])([OX1-])([#6])[#6])]"),
  list(name = "Sulfoxide", smarts = "[$([SX3](=[OX1])([#6])[#6]),$([SX3+]([OX1-])([#6])[#6])]"),
  list(name = "Sulfonium", smarts = "[S+;!$([S]~[!#6]);!$([S]*~[#7,#8,#15,#16])]"),
  list(name = "Sulfuric_acid", smarts = "[SX4](=[OX1])(=[OX1])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]"),
  list(name = "Sulfuric_monoester", smarts = "[SX4](=[OX1])(=[OX1])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Sulfuric_diester", smarts = "[SX4](=[OX1])(=[OX1])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Sulfuric_monoamide", smarts = "[SX4](=[OX1])(=[OX1])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[$([OX2H]),$([OX1-])]"),
  list(name = "Sulfuric_diamide", smarts = "[SX4](=[OX1])(=[OX1])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Sulfuric_esteramide", smarts = "[SX4](=[OX1])(=[OX1])([#7X3][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Sulfonic_acid", smarts = "[SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[$([OX2H]),$([OX1-])]"),
  list(name = "Sulfonamide", smarts = "[SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Sulfonic_ester", smarts = "[SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Sulfonic_halide", smarts = "[SX4;$([H1]),$([H0][#6])](=[OX1])(=[OX1])[FX1,ClX1,BrX1,IX1]"),

  list(name = "Sulfinic_acid", smarts = "[SX3;$([H1]),$([H0][#6])](=[OX1])[$([OX2H]),$([OX1-])]"),
  list(name = "Sulfinic_amide", smarts = "[SX3;$([H1]),$([H0][#6])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Sulfinic_ester", smarts = "[SX3;$([H1]),$([H0][#6])](=[OX1])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Sulfinic_halide", smarts = "[SX3;$([H1]),$([H0][#6])](=[OX1])[FX1,ClX1,BrX1,IX1]"),
  list(name = "Sulfenic_acid", smarts = "[SX2;$([H1]),$([H0][#6])][$([OX2H]),$([OX1-])]"),
  list(name = "Sulfenic_amide", smarts = "[SX2;$([H1]),$([H0][#6])][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Sulfenic_ester", smarts = "[SX2;$([H1]),$([H0][#6])][OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Sulfenic_halide", smarts = "[SX2;$([H1]),$([H0][#6])][FX1,ClX1,BrX1,IX1]"),
  list(name = "Phosphine", smarts = "[PX3;$([H3]),$([H2][#6]),$([H1]([#6])[#6]),$([H0]([#6])([#6])[#6])]"),
  list(name = "Phosphine_oxide", smarts = "[PX4;$([H3]=[OX1]),$([H2](=[OX1])[#6]),$([H1](=[OX1])([#6])[#6]),$([H0](=[OX1])([#6])([#6])[#6])]"),
  list(name = "Phosphonium", smarts = "[P+;!$([P]~[!#6]);!$([P]*~[#7,#8,#15,#16])]"),
  list(name = "Phosphorylen", smarts = "[PX4;$([H3]=[CX3]),$([H2](=[CX3])[#6]),$([H1](=[CX3])([#6])[#6]),$([H0](=[CX3])([#6])([#6])[#6])]"),
  list(name = "Phosphonic_acid", smarts = "[PX4;$([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]"),
  list(name = "Phosphonic_monoester", smarts = "[PX4;$([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Phosphonic_diester", smarts = "[PX4;$([H1]),$([H0][#6])](=[OX1])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Phosphonic_monoamide", smarts = "[PX4;$([H1]),$([H0][#6])](=[OX1])([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphonic_diamide", smarts = "[PX4;$([H1]),$([H0][#6])](=[OX1])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphonic_esteramide", smarts = "[PX4;$([H1]),$([H0][#6])](=[OX1])([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphoric_acid", smarts = "[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]"),
  list(name = "Phosphoric_monoester", smarts = "[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Phosphoric_diester", smarts = "[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Phosphoric_triester", smarts = "[PX4D4](=[OX1])([OX2][#6;!$(C=[O,N,S])])([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Phosphoric_monoamide", smarts = "[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphoric_diamide", smarts = "[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphoric_triamide", smarts = "[PX4D4](=[OX1])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphoric_monoestermonoamide", smarts = "[PX4D4](=[OX1])([$([OX2H]),$([OX1-])])([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphoric_diestermonoamide", smarts = "[PX4D4](=[OX1])([OX2][#6;!$(C=[O,N,S])])([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphoric_monoesterdiamide", smarts = "[PX4D4](=[OX1])([OX2][#6;!$(C=[O,N,S])])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphinic_acid", smarts = "[PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[$([OX2H]),$([OX1-])]"),
  list(name = "Phosphinic_ester", smarts = "[PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[OX1])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Phosphinic_amide", smarts = "[PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])]"),
  list(name = "Phosphonous_acid", smarts = "[PX3;$([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[$([OX2H]),$([OX1-])]"),
  list(name = "Phosphonous_monoester", smarts = "[PX3;$([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Phosphonous_diester", smarts = "[PX3;$([H1]),$([H0][#6])]([OX2][#6;!$(C=[O,N,S])])[OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Phosphonous_monoamide", smarts = "[PX3;$([H1]),$([H0][#6])]([$([OX2H]),$([OX1-])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphonous_diamide", smarts ="[PX3;$([H1]),$([H0][#6])]([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])([#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])])"), # modified
  list(name = "Phosphonous_esteramide", smarts = "[PX3;$([H1]),$([H0][#6])]([OX2][#6;!$(C=[O,N,S])])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Phosphinous_acid", smarts = "[PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][$([OX2H]),$([OX1-])]"),
  list(name = "Phosphinous_ester", smarts = "[PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][OX2][#6;!$(C=[O,N,S])]"),
  list(name = "Phosphinous_amide", smarts = "[PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
  list(name = "Quart_silane", smarts = "[SiX4]([#6])([#6])([#6])[#6]"),
  list(name = "Non-quart_silane", smarts = "[SiX4;$([H1]([#6])([#6])[#6]),$([H2]([#6])[#6]),$([H3][#6]),$([H4])]"),
  list(name = "Silylmonohalide", smarts = "[SiX4]([FX1,ClX1,BrX1,IX1])([#6])([#6])[#6]"),
  list(name = "Het_trialkylsilane", smarts = "[SiX4]([!#6])([#6])([#6])[#6]"),
  list(name = "Dihet_dialkylsilane", smarts = "[SiX4]([!#6])([!#6])([#6])[#6]"),
  list(name = "Trihet_alkylsilane", smarts = "[SiX4]([!#6])([!#6])([!#6])[#6]"),
  list(name = "Trialkylborane", smarts = "[BX3]([#6])([#6])[#6]"),
  list(name = "Boric_acid_derivatives", smarts = "[BX3]([!#6])([!#6])[!#6]"),
  list(name = "Boronic_acid_derivative", smarts = "[BX3]([!#6])([!#6])[!#6]"),
  list(name = "Borohydride", smarts = "[BH1,BH2,BH3,BH4]"),
  list(name = "Quaternary_boron", smarts = "[BX4]"),
  list(name = "Aromatic", smarts = "a"),
  list(name = "Heterocyclic", smarts = "[!#6;!R0]"),
  list(name = "Epoxide", smarts = "[OX2r3]1[#6r3][#6r3]1"),
  list(name = "NH_aziridine", smarts = "[NX3H1r3]1[#6r3][#6r3]1"),
  list(name = "Spiro", smarts = "[D4R;$(*(@*)(@*)(@*)@*)]"),
  list(name = "Annelated_rings", smarts = "[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]@[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]"),
  list(name = "Bridged_rings", smarts = "[R;$(*(@*)(@*)@*);!$([D4R;$(*(@*)(@*)(@*)@*)]);!$([R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])]@[R;$(*(@*)(@*)@*);!$([R2;$(*(@*)(@*)(@*)@*)])])]"),
  list(name = "Sugar_pattern_1", smarts = "[OX2;$([r5]1@C@C@C(O)@C1),$([r6]1@C@C@C(O)@C(O)@C1)]"),
  list(name = "Sugar_pattern_2", smarts = "[OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]"),
  list(name = "Sugar_pattern_2_reducing", smarts = "[OX2;$([r5]1@C(!@[OX2H1])@C@C@C1),$([r6]1@C(!@[OX2H1])@C@C@C@C1)]"),
  list(name = "Conjugated_double_bond", smarts = "*=*[*]=,#,:[*]"),
  list(name = "Conjugated_tripple_bond", smarts = "*#*[*]=,#,:[*]"),
  list(name = "Mixed_anhydrides", smarts = "[$(*=O),$([#16,#14,#5]),$([#7]([#6]=[OX1]))][#8X2][$(*=O),$([#16,#14,#5]),$([#7]([#6]=[OX1]))]"),
  list(name = "Halogen_on_hetero", smarts = "[FX1,ClX1,BrX1,IX1][!#6]"),
  list(name = "Halogen_multi_subst", smarts = "[F,Cl,Br,I;!$([X1]);!$([X0-])]"),
  list(name = "Trifluoromethyl", smarts = "[FX1][CX4;!$([H0][Cl,Br,I]);!$([F][C]([F])([F])[F])]([FX1])([FX1])"),
 # list(name = "C_ONS_bond", smarts = "[#6]~[#7,#8,#16]"),
  list(name = "Anion", smarts = "[-1,-2,-3,-4,-5,-6,-7]"),
  list(name = "Kation", smarts = "[+1,+2,+3,+4,+5,+6,+7]"),
  list(name = "Dicarbodiazene", smarts = "[CX3](=[OX1])[NX2]=[NX2][CX3](=[OX1])"),
  list(name = "CH-acidic", smarts = "[$([CX4;!$([H0]);!$(C[!#6;!$([P,S]=O);!$(N(~O)~O)])][$([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-]);!$(*[S,O,N;H1,H2]);!$([*+0][S,O;X1-])]),$([CX4;!$([H0])]1[CX3]=[CX3][CX3]=[CX3]1)]"),
  list(name = "CH-acidic_strong", smarts = "[CX4;!$([H0]);!$(C[!#6;!$([P,S]=O);!$(N(~O)~O)])]([$([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-]);!$(*[S,O,N;H1,H2]);!$([*+0][S,O;X1-])])[$([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-]);!$(*[S,O,N;H1,H2]);!$([*+0][S,O;X1-])]")
)

# removed: 
# list(name = "Amine", smarts = "[NX3+0,NX4+;!$([N]~[!#6]);!$([N]*~[#7,#8,#15,#16])]"),
 # list(name = "Sulfuric_derivative", smarts = "[SX4D4](=[!#6])(=[!#6])([!#6])[!#6]"),
  #list(name = "Phosphinous_derivatives", smarts = "[PX3;$([H2]),$([H1][#6]),$([H0]([#6])[#6])][!#6]"),
# list(name = "Sugar_pattern_combi", smarts = "[OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C(O)@C1)]"),
# list(name = "Sugar_pattern_2_alpha", smarts = "[OX2;$([r5]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]"),
# list(name = "Sugar_pattern_2_beta", smarts = "[OX2;$([r5]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]"),
# list(name = "Carbonic_acid_derivatives", smarts = "[!#6][#6X3](=[!#6])[!#6]"),
#  list(name = "Chiral_center_specified", smarts = "[$([*@](~*)(~*)(*)*),$([*@H](*)(*)*),$([*@](~*)(*)*),$([*@H](~*)~*)]")
# Charged
#   list(name = "1,3-Tautomerizable", smarts = "[$([#7X2,OX1,SX1]=*[!H0;!$([a;!n])]),$([#7X3,OX2,SX2;!H0]*=*),$([#7X3,OX2,SX2;!H0]*:n)]"),
#   list(name = "1,5-Tautomerizable", smarts = "[$([#7X2,OX1,SX1]=,:**=,:*[!H0;!$([a;!n])]),$([#7X3,OX2,SX2;!H0]*=**=*),$([#7X3,OX2,SX2;!H0]*=,:**:n)]"),
#   list(name = "Rotatable_bond", smarts = "[!$(*#*)&!D1]-!@[!$(*#*)&!D1]"),
#   list(name = "Michael_acceptor", smarts = "[CX3]=[CX3][$([CX3]=[O,N,S]),$(C#[N]),$([S,P]=[OX1]),$([NX3]=O),$([NX3+](=O)[O-])]"),
#   #list(name = "Cis_double_bond", smarts = "*/[D2]=[D2]\\*"),
#   #list(name = "Trans_double_bond", smarts = "*/[D2]=[D2]/*"),
# #list(name = "Amide", smarts = #"[CX3;$([R0][#6]),$([H1R0])](=[OX1])[#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N#,S])])]"),
#   list(name = "Vinylogous_carbonyl_or_carboxyl_derivative", smarts = "[#6X3](=[OX1])[#6X3]=,:[#6X3][#7,#8,#16,F,Cl,Br,I]"),
#   list(name = "Vinylogous_acid", smarts = "[#6X3](=[OX1])[#6X3]=,:[#6X3][$([OX2H]),$([OX1-])]"),
#   list(name = "Vinylogous_ester", smarts = "[#6X3](=[OX1])[#6X3]=,:[#6X3][#6;!$(C=[O,N,S])]"),
#   list(name = "Vinylogous_amide", smarts = "[#6X3](=[OX1])[#6X3]=,:[#6X3][#7X3;$([H2]),$([H1][#6;!$(C=[O,N,S])]),$([#7]([#6;!$(C=[O,N,S])])[#6;!$(C=[O,N,S])])]"),
#   list(name = "Vinylogous_halide", smarts = "[#6X3](=[OX1])[#6X3]=,:[#6X3][FX1,ClX1,BrX1,IX1]"),
#   list(name = "Alcohol", smarts = "[OX2H][CX4;!$(C([OX2H])[O,S,#7,#15])]"),
#   list(name = "Acylhalide", smarts = "[CX3;$([R0][#6]),$([H1R0])](=[OX1])[FX1,ClX1,BrX1,IX1]"),
#   list(name = "Carboxylic_acid_derivative", smarts = "[$([#6X3H0][#6]),$([#6X3H])](=[!#6])[!#6]"),  
#   list(name = "Sulfonic_derivative", smarts = "[SX4;$([H1]),$([H0][#6])](=[!#6])(=[!#6])[!#6]"),
#   list(name = "Sulfinic_derivative", smarts = "[SX3;$([H1]),$([H0][#6])](=[!#6])[!#6]"),
#   list(name = "Sulfenic_derivative", smarts = "[SX2;$([H1]),$([H0][#6])][!#6]"),
#   list(name = "Phosphonic_acid_derivative", smarts = "[PX4;$([H1]),$([H0][#6])](=[!#6])([!#6])[!#6]"),
#   list(name = "Phosphoric_acid_derivative", smarts = "[PX4D4](=[!#6])([!#6])([!#6])[!#6]"),
#   list(name = "Phosphinic_acid_derivative", smarts = "[PX4;$([H2]),$([H1][#6]),$([H0]([#6])[#6])](=[!#6])[!#6]"), 
#   list(name = "Phosphonous_derivatives", smarts = "[PX3;$([D2]),$([D3][#6])]([!#6])[!#6]"),
#   list(name = "Silicic_acid_derivative", smarts = "[SiX4]([!#6])([!#6])([!#6])[!#6]"),
  
fg_hierarchy <- FunctionalGroups$BuildFuncGroupHierarchy()

fg_hierarchy <- fg_hierarchy[[1]]
fg_hierarchy <- extend_fg_hierarchy(fg_hierarchy, custom_groups)
fg_hierarchy <- fg_hierarchy[-1]

Functional groups

Code 
# Get functional group names and SMARTS patterns
fg_list <- lapply(fg_hierarchy, function(fg) {
  list(name = fg$name, smarts = fg$smarts)
})
fg_names <- sapply(fg_list, `[[`, "name")
fg_smarts <- sapply(fg_list, function(fg) Chem$MolFromSmarts(fg$smarts))

get_fg_counts <- function(smile) {
  mol <- Chem$MolFromSmiles(smile)
  if (is.null(mol)) {
    return(rep(NA_integer_, length(fg_smarts)))
  }
  sapply(fg_smarts, function(smarts_mol) {
    matches <- mol$GetSubstructMatches(smarts_mol)
    length(matches)
  })
}

analyze_smiles_vector <- function(smiles_vector) {
  fg_matrix <- t(sapply(smiles_vector, get_fg_counts))
  colnames(fg_matrix) <- fg_names
  result_df <- as_tibble(fg_matrix)
  result_df <- bind_cols(tibble(SMILES = smiles_vector), result_df)
  return(result_df)
}

fg_df <- analyze_smiles_vector(smiles$smiles)
fg_df<-fg_df%>%mutate(id1 = smiles$ID,
                      id2 = smiles$ID, .before = SMILES)
write.csv(fg_df, file = here(data_deliv_dir,"smarts_functional_groups.csv"), row.names = FALSE)

Maximum Common Substructure

Code 
library(reticulate)
library(future.apply)

smiles_vec <- smiles$smiles  
pairs <- combn(seq_along(smiles_vec), 2, simplify = FALSE)
plan(multisession, workers = 20)  

results_list <- future_lapply(pairs, function(idx_pair) {
  
  library(reticulate)
  library(here)
  source_python(here("scripts/mcs_single_maxfragment.py"))  # re-import inside worker
  
  i <- idx_pair[1]
  j <- idx_pair[2]
  
  mcs_size <- compute_mcs_and_fragment_diff(smiles_vec[i], smiles_vec[j])
  
  list(mol1_index = i, mol2_index = j, mcs_size = mcs_size)
}, future.seed = TRUE)

# Bind all results
results <- do.call(rbind, lapply(results_list, as.data.frame))
write.csv(results, file = here(data_deliv_dir,"results_table_max_frag_size.csv"), row.names = FALSE)

Subsets

Code 
results_selected <- results %>%
  mutate(crit = mcs_size)%>%
  group_by(mol1_index) %>%
  slice(which.min(crit))

MCS Subsets

Code 
# Extract the vectors
rows <- smiles$smiles[results_selected$mol1_index]
cols <- smiles$smiles[results_selected$mol2_index]

comparison_table <- purrr::map2_df(rows, cols, compare_smiles_pair,
                                   .progress = list(
  type = "iterator", 
  format = "Calculating {cli::pb_bar} {cli::pb_percent} {cli::pb_current}/{cli::pb_total}",
  clear = FALSE))

comparison_table$are_similar <- as.double(purrr::map2_lgl(comparison_table$common1, comparison_table$common2, are_smiles_identical))

comparison_table$similarity = results_selected$crit
comparison_table$id1 = results_selected$mol1_index
comparison_table$id2 = results_selected$mol2_index

write.csv(comparison_table, file = here(data_deliv_dir,"comparison_table.csv"), row.names = FALSE)

Add membership groups

Code 
results_selected <- results_selected %>% select(-any_of("group"))
results_selected_crit<-results_selected %>% filter(crit<7) 

uid = unique(c(results_selected_crit$mol1_index,results_selected_crit$mol2_index))
nodes <- data.frame(id = uid,label = paste(uid))
edges <- data.frame(from = results_selected_crit$mol1_index,
                    to = results_selected_crit$mol2_index, 
                    width =results_selected_crit$crit,
                    label = paste(results_selected_crit$crit))
g <- graph_from_data_frame(d = edges, vertices = nodes, directed = FALSE)
components <- components(g, mode = "weak")
nodes$group <- components$membership

nodes$atom_count <- unlist(lapply(smiles$smiles[nodes$id], get_atom_count)) 

results_selected <- results_selected%>%
  mutate(id=mol1_index) %>%
  left_join(nodes) %>%
   select(-c(label, id)) %>%
  mutate(group = ifelse(is.na(group), 0, group))

tabulate(results_selected$group+1)
 [1] 299  16 169  23   9  38  26   2   4 118   6   7   7   2   2  34  12  15   2
[20]   3   2   2   2   2   3   3  15   2   3   3   2   3   2   5   3   2   3   3
[39]   2   2   2   9   3   6  15   8   3   2   2   2   3  11   3   2   5   2   4
[58]   4   3   2   3   2   4   2   2   2   2   3   3   4   2   2   2   3   2   2
[77]   2   2   3   2   2   2   2   2   3   4   6   2   2   2

Visualise Network

Code 
visNetwork(nodes, edges, width = "100%")

Orient graph

Code 
orient_graph_no_multiple_incoming <- function(g) {
  stopifnot(!is_directed(g))
  
  degs <- degree(g)
  node_order <- names(sort(degs, decreasing = TRUE))
  
  g_directed <- make_empty_graph(n = vcount(g), directed = TRUE)
  V(g_directed)$name <- V(g)$name
  
  has_parent <- setNames(rep(FALSE, vcount(g)), V(g)$name)
  
  for (node in node_order) {
    neighbors_node <- neighbors(g, node, mode = "all")
    
    for (nbr in neighbors_node) {
      nbr_name <- V(g)[nbr]$name
      
      # Only consider edge if neighbor has no incoming edge
      if (!has_parent[nbr_name] && node != nbr_name) {
        
        # Check if adding edge would introduce a cycle
        temp_graph <- add_edges(g_directed, c(node, nbr_name))
        if (is_dag(temp_graph)) {
          g_directed <- temp_graph
          has_parent[nbr_name] <- TRUE
        }
      }
    }
  }
  
  return(g_directed)
}

# Apply it
g_directed <- orient_graph_no_multiple_incoming(g)

Visualise Network

Code 
# Create nodes data frame
nodes <- data.frame(
  id = V(g_directed)$name,
  label = V(g_directed)$name,
  stringsAsFactors = FALSE
)

components <- components(g, mode = "weak")
nodes$group <- components$membership

# Create edges data frame
edges <- igraph::as_data_frame(g_directed, what = "edges")
colnames(edges) <- c("from", "to")

#nodes with no outgoing edges
nodes_noin <- V(g_directed)[degree(g_directed, mode = "in") == 0]
nodes_noin <- names(nodes_noin)

visNetwork(nodes, edges, width = "100%") %>%
  visEdges(arrows = "to")

Equation output:

Code 
topo_order <- topo_sort(g_directed, mode = "out")
topo_order <- names(topo_order)

# Initialize a named list to store equations
equations <- setNames(vector("list", length(topo_order)), topo_order)

for (node in topo_order) {
  parents <- names(neighbors(g_directed, node, mode = "in"))
  
  if (length(parents) == 0) {
    # If no parents, it's a root node
    equations[[node]] <- node
  } else {
    # Sum of parents
    equations[[node]] <- paste0(node, " = ", paste(parents, collapse = " + "))
  }
}

# Print all equations
equations_vec <- unlist(equations)
cat(paste(equations_vec, collapse = "\n"))

Plot

Code 
plotting_i = function(i, .ilist) {
  data %>% 
    filter(ID %in% c(.ilist$id1[i], .ilist$id2[i])) %>%
    ggplot(aes(x = fi, y = logk, group = ID)) + 
    geom_line(aes(color = logP_ACD)) + 
    labs(
      title = paste(analytes_names$Analyte[.ilist$id1[i]], "\n", analytes_names$Analyte[.ilist$id2[i]]), 
      x = "\u03C6", 
      y = expression(log~k[obs])
    ) + 
    theme_gray(base_size = 10) + 
    theme(legend.position = "none")+
    theme(plot.title = element_text(size = 5), 
          axis.title = element_text(size = 7),
          axis.text = element_text(size = 5))
}

list0 = comparison_table%>% filter(similarity==0)
list1 = comparison_table%>% filter(similarity==1)
list2 = comparison_table%>% filter(similarity==2)
list10 = comparison_table%>% filter(similarity==10)
map(1:min(20, nrow(list0)), \(x) plotting_i(x, list0)) %>% wrap_plots(ncol = 4)

Code 
map(1:min(20, nrow(list1)), \(x) plotting_i(x, list1)) %>% wrap_plots(ncol = 4)

Code 
map(1:min(20, nrow(list2)), \(x) plotting_i(x, list2)) %>% wrap_plots(ncol = 4)

Code 
map(1:min(20, nrow(list10)), \(x) plotting_i(x, list10)) %>% wrap_plots(ncol = 4)

Add or remove functional groups

Remove

Code 
# Extract the vectors
idx1 = results_selected_crit$mol1_index
idx2 = results_selected_crit$mol2_index

comparison_table_remove <- purrr::map2_df(idx1, idx2, \(x,y) extract_diff_fragments_combined(x, y, smiles$smiles, mcs_params, fg_hierarchy),
                                   .progress = list(type = "iterator", 
  format = "Calculating {cli::pb_bar} {cli::pb_percent} {cli::pb_current}/{cli::pb_total}",
  clear = FALSE))

write.csv(comparison_table_remove, file = here(data_deliv_dir,"comparison_table_remove.csv"), row.names = FALSE)

Add

Code 
# Extract the vectors
idx1 = results_selected_crit$mol1_index
idx2 = results_selected_crit$mol2_index

comparison_table_add <-  purrr::map2_df(idx2, idx1, \(x,y) extract_diff_fragments_combined(x, y, smiles$smiles, mcs_params, fg_hierarchy),
                                   .progress = list(type = "iterator", 
  format = "Calculating {cli::pb_bar} {cli::pb_percent} {cli::pb_current}/{cli::pb_total}",
  clear = FALSE))

write.csv(comparison_table_add, file = here(data_deliv_dir,"comparison_table_add.csv"), row.names = FALSE)

Print

Code 
comparison_table_remove %>%
  kbl(escape = FALSE, format = "html", align = "l") %>%
  kable_styling(full_width = FALSE, position = "center", bootstrap_options = c("striped", "hover", "condensed"))
atom_idx atom_symbol matched_fg frag_smiles frag_id idx1 idx2
11 O Carboxylic_acid O 1 1 101
12 O Carboxylic_acid O 2 1 101
13 N Primary_arom_amine N 3 1 101
7 O Carboxylic_acid, Conjugated_double_bond O 1 2 11
8 O Carboxylic_acid O 2 2 11
9 N Primary_arom_amine N 3 2 11
0 C NA C 1 3 356
0 C Primary_carbon C 1 4 5
10 C Primary_carbon C 2 4 5
0 C Carboxylic_ester CO 1 5 95
1 O Carboxylic_ester CO 1 5 95
3 O Carboxylic_ester O 2 5 95
8 C Carboxylic_ester C 3 5 95
9 O Secondary_alcohol, 1,2-Aminoalcohol O 1 7 415
0 C Alkene C=C 1 8 11
1 C Secondary_carbon, Alkene C=C 1 8 11
10 C Alkylarylether C 2 8 11
11 O Phenol O 3 8 11
6 O Secondary_alcohol, 1,2-Diol O 1 9 11
8 O Secondary_alcohol, 1,2-Diol O 2 9 11
10 O Secondary_alcohol, 1,2-Diol O 3 9 11
11 O Secondary_alcohol, 1,2-Diol O 4 9 11
2 C Primary_alcohol CO 1 10 83
3 O Primary_alcohol CO 1 10 83
8 O Oxoarene, Conjugated_double_bond O 2 10 83
9 O Phenol O 3 10 83
0 C Primary_carbon C 1 11 13
0 C Primary_carbon, Secondary_carbon CC 1 12 57
1 C Primary_carbon, Secondary_carbon, Quaternary_carbon CC 1 12 57
3 C Quaternary_carbon, Aromatic c1ccccc1 2 12 57
4 C Aromatic c1ccccc1 2 12 57
5 C Aromatic c1ccccc1 2 12 57
6 C Aromatic c1ccccc1 2 12 57
7 C Aromatic c1ccccc1 2 12 57
8 C Aromatic c1ccccc1 2 12 57
10 O NA O 3 12 57
13 O Urea O 4 12 57
16 O NA O 5 12 57
4 C Primary_alcohol, 1,2-Diol CO 1 14 95
5 O Primary_alcohol, 1,2-Diol CO 1 14 95
7 O Secondary_alcohol, 1,2-Diol O 2 14 95
8 O Secondary_alcohol, 1,2-Diol O 3 14 95
9 O Primary_alcohol, 1,2-Diol O 4 14 95
10 C NA CC=CCO 1 15 608
11 C Tertiary_carbon, Alkene, Annelated_rings CC=CCO 1 15 608
12 C Alkene CC=CCO 1 15 608
13 C Dialkylether CC=CCO 1 15 608
14 O Dialkylether, Heterocyclic CC=CCO 1 15 608
18 O Lactam O 2 15 608
20 C Tertiary_carbon, Quaternary_carbon, Annelated_rings C 3 15 608
0 C Primary_carbon C 1 16 522
11 O Secondary_alcohol O 2 16 522
16 O Lactam, Oxoarene, Conjugated_double_bond O 3 16 522
11 O Phenol O 1 17 87
8 O Carboxylic_acid O 1 19 556
9 O Carboxylic_acid O 2 19 556
11 C Secondary_carbon, Primary_amide NC=O 1 20 943
12 O Primary_amide NC=O 1 20 943
13 N Primary_amide NC=O 1 20 943
0 C Primary_carbon, Secondary_carbon CC 1 21 972
1 C Primary_carbon, Secondary_carbon CC 1 21 972
0 C Primary_carbon, Secondary_carbon C 1 23 29
3 C Primary_carbon, Tertiary_carbon C 2 23 29
7 C Primary_carbon C 1 25 26
8 O Secondary_alcohol O 2 25 26
0 C Primary_carbon, Secondary_carbon CC 1 27 219
1 C Primary_carbon, Secondary_carbon CC 1 27 219
3 O Secondary_amide O 2 27 219
6 C Primary_carbon C 3 27 219
7 C Carboxylic_acid O=CO 4 27 219
8 O Carboxylic_acid O=CO 4 27 219
9 O Carboxylic_acid O=CO 4 27 219
17 Cl Arylchloride Cl 5 27 219
18 Cl Arylchloride Cl 6 27 219
19 Cl Arylchloride Cl 7 27 219
0 C Dialkylthioether CS 1 28 29
1 S Dialkylthioether CS 1 28 29
15 O Carboxylic_acid O 1 29 30
16 O Carboxylic_acid O 2 29 30
0 C Primary_carbon CCO 1 30 278
1 C Primary_carbon, Secondary_alcohol CCO 1 30 278
3 C Carboxylic_acid O=CO 2 30 278
4 O Carboxylic_acid O=CO 2 30 278
5 O Carboxylic_acid O=CO 2 30 278
17 Cl Arylchloride Cl 3 30 278
18 Cl Arylchloride Cl 4 30 278
19 Cl Arylchloride Cl 5 30 278
20 O Secondary_alcohol CCO 1 30 278
0 C Primary_carbon CC 1 31 32
1 C Primary_carbon CC 1 31 32
8 O Lactam O 1 32 35
9 S Isothiourea, Arylthiol S 1 33 868
9 N Nitrile N 1 34 55
9 Cl Arylchloride Cl 1 35 38
0 C Primary_carbon, CH-acidic C 1 36 37
2 O Carboxylic_ester O 2 36 37
9 N Primary_arom_amine N 1 38 45
13 C Aromatic cc[nH] 1 39 911
14 C Aromatic cc[nH] 1 39 911
15 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic cc[nH] 1 39 911
0 C Alkylarylether CO 1 40 43
1 O Alkylarylether CO 1 40 43
9 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 1 41 43
10 O Anion O=[NH+][O-] 1 41 43
11 O Conjugated_double_bond O=[NH+][O-] 1 41 43
0 C Aromatic c1ccccc1 1 42 57
1 C Aromatic c1ccccc1 1 42 57
2 C Aromatic c1ccccc1 1 42 57
3 C Aromatic c1ccccc1 1 42 57
4 C Aromatic c1ccccc1 1 42 57
5 C Aromatic c1ccccc1 1 42 57
9 C Nitrile, Conjugated_tripple_bond C#N 1 43 44
10 N Nitrile, Conjugated_tripple_bond C#N 1 43 44
0 C Alkylarylether CO 1 44 45
1 O Alkylarylether CO 1 44 45
6 C Aromatic cn[nH] 1 47 49
7 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cn[nH] 1 47 49
8 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic cn[nH] 1 47 49
9 O Ketone, Conjugated_double_bond O 1 48 70
10 O Aldehyde, Conjugated_double_bond O 1 50 51
10 O Carboxylic_acid, Conjugated_double_bond O 1 52 71
11 O Carboxylic_acid O 2 52 71
9 C Carboxylic_acid, Conjugated_double_bond O=CO 1 53 71
10 O Carboxylic_acid, Conjugated_double_bond O=CO 1 53 71
11 O Carboxylic_acid O=CO 1 53 71
0 C Primary_carbon, CH-acidic CC(=O)O 1 54 55
1 C Primary_carbon, Carboxylic_ester CC(=O)O 1 54 55
2 O Carboxylic_ester CC(=O)O 1 54 55
3 O Carboxylic_ester CC(=O)O 1 54 55
0 C Primary_carbon C 1 56 635
5 O Carboxylic_acid O 2 56 635
6 O Carboxylic_acid O 3 56 635
0 C Primary_carbon CC=C(C)C 1 57 463
1 C Primary_carbon, Alkene CC=C(C)C 1 57 463
2 C Alkene CC=C(C)C 1 57 463
3 C NA CC=C(C)C 1 57 463
14 C Primary_carbon CC=C(C)C 1 57 463
13 C Secondary_carbon, Aromatic c1c[nH]cn1 1 59 60
14 C Aromatic c1c[nH]cn1 1 59 60
15 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic c1c[nH]cn1 1 59 60
16 C Aromatic c1c[nH]cn1 1 59 60
17 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1c[nH]cn1 1 59 60
0 C Dialkylthioether CS 1 61 63
1 S Dialkylthioether CS 1 61 63
9 O Secondary_amide O 1 62 600
13 O Primary_alcohol O 2 62 600
14 C Carboxylic_acid O=CO 3 62 600
15 O Carboxylic_acid O=CO 3 62 600
16 O Carboxylic_acid O=CO 3 62 600
0 C Primary_carbon, CH-acidic CC(=O)O 1 68 69
1 C Primary_carbon, Carboxylic_ester CC(=O)O 1 68 69
2 O Carboxylic_ester CC(=O)O 1 68 69
3 O Carboxylic_ester CC(=O)O 1 68 69
13 O NA CC(=O)O 2 68 69
14 C Primary_carbon CC(=O)O 2 68 69
15 O NA CC(=O)O 2 68 69
16 C Primary_carbon, CH-acidic CC(=O)O 2 68 69
8 O Carboxylic_acid O 1 69 71
13 Cl Arylchloride Cl 2 69 71
14 Cl Arylchloride Cl 3 69 71
10 O Carboxylic_acid O 1 70 653
11 O Carboxylic_acid O 2 70 653
13 Cl Arylchloride Cl 1 72 73
10 Cl Arylchloride Cl 1 73 74
11 Cl Arylchloride Cl 2 73 74
10 Cl Arylchloride Cl 1 74 75
0 C Primary_carbon C 1 75 76
14 Cl Arylchloride Cl 2 75 76
13 Cl Arylchloride Cl 1 76 77
13 Cl Arylchloride Cl 1 77 78
6 O Carboxylic_acid O 1 78 377
7 O Carboxylic_acid O 2 78 377
13 Cl Arylchloride Cl 3 78 377
23 O Secondary_alcohol O 1 79 81
10 C Alkene C=CCO 1 80 81
11 C Alkene C=CCO 1 80 81
12 C Quaternary_carbon, Secondary_alcohol C=CCO 1 80 81
23 O Secondary_alcohol C=CCO 1 80 81
0 C Alkene C 1 81 553
4 C Secondary_carbon, Tertiary_carbon, Quaternary_carbon C 2 81 553
14 C Primary_carbon, Quaternary_carbon C 3 81 553
17 C Tertiary_carbon, Carboxylic_acid O=CO 4 81 553
18 O Carboxylic_acid O=CO 4 81 553
19 O Carboxylic_acid O=CO 4 81 553
20 C Quaternary_carbon, Lactone O=CO 5 81 553
21 O Lactone O=CO 5 81 553
22 O Lactone, Heterocyclic O=CO 5 81 553
8 O Phenol, 1,2-Diphenol O 1 86 90
6 C Carboxylic_acid, Conjugated_double_bond O=CO 1 88 481
7 O Carboxylic_acid, Conjugated_double_bond O=CO 1 88 481
8 O Carboxylic_acid O=CO 1 88 481
5 O Urea, Oxoarene, Conjugated_double_bond O 1 89 230
8 O Lactam, Oxoarene, Conjugated_double_bond O 2 89 230
0 C Alkylarylether CO 1 90 99
1 O Alkylarylether CO 1 90 99
8 O Phenol O 2 90 99
11 O Carboxylic_acid O 3 90 99
1 C Alkene, Conjugated_double_bond CC(=O)O 1 91 95
2 C Carboxylic_acid, Conjugated_double_bond CC(=O)O 1 91 95
3 O Carboxylic_acid, Conjugated_double_bond CC(=O)O 1 91 95
4 O Carboxylic_acid CC(=O)O 1 91 95
0 C Primary_carbon CCC 1 93 94
1 C Primary_carbon, Alkene CCC 1 93 94
6 C Alkene CCO 2 93 94
7 C Primary_alcohol CCO 2 93 94
8 O Primary_alcohol CCO 2 93 94
10 C Primary_carbon CCC 1 93 94
1 C Secondary_carbon, Carboxylic_acid O=CO 1 94 95
2 O Carboxylic_acid O=CO 1 94 95
3 O Carboxylic_acid O=CO 1 94 95
10 O Carboxylic_acid, Alpha_hydroxyacid O 2 94 95
11 O Carboxylic_acid, Alpha_hydroxyacid O 3 94 95
12 O Tertiary_alcohol, Alpha_hydroxyacid O 4 94 95
2 C Primary_carbon, Tertiary_carbon C 1 95 1016
7 N Primary_aliph_amine, Alpha_aminoacid N 2 95 1016
0 C Primary_carbon C 1 97 98
0 C Primary_carbon, Secondary_carbon C 1 98 116
0 C NA C 1 100 380
9 O Imidoacid O 2 100 380
0 C Primary_carbon CCNCC 1 116 361
1 C Primary_carbon, Tertiary_amide CCNCC 1 116 361
2 N Tertiary_amide CCNCC 1 116 361
3 C Primary_carbon, Tertiary_amide CCNCC 1 116 361
4 C Primary_carbon CCNCC 1 116 361
7 C Primary_carbon, CH-acidic C 2 116 361
0 C Alkene C 1 117 121
10 O Phenol O 1 118 943
11 O Phenol O 2 118 943
0 C Primary_carbon C 1 119 955
12 N Primary_arom_amine N 2 119 955
0 C Aromatic c1ccccc1 1 120 349
1 C Aromatic c1ccccc1 1 120 349
2 C Aromatic c1ccccc1 1 120 349
3 C Aromatic c1ccccc1 1 120 349
4 C Aromatic c1ccccc1 1 120 349
5 C Aromatic c1ccccc1 1 120 349
0 C Primary_carbon CCO 1 121 202
1 C Primary_carbon, Acetal CCO 1 121 202
2 O Acetal, Acetal_like CCO 1 121 202
12 O Acetal, Acetal_like CCO 2 121 202
13 C Primary_carbon, Acetal CCO 2 121 202
14 C Primary_carbon CCO 2 121 202
13 C Ketone, Aromatic, Conjugated_double_bond c1ccccc1 1 123 913
14 C Aromatic, Conjugated_double_bond c1ccccc1 1 123 913
15 C Aromatic c1ccccc1 1 123 913
16 C Aromatic c1ccccc1 1 123 913
17 C Aromatic c1ccccc1 1 123 913
18 C Aromatic, Conjugated_double_bond c1ccccc1 1 123 913
0 C Primary_carbon, Secondary_carbon CC 1 124 363
1 C Primary_carbon, Secondary_carbon CC 1 124 363
7 C Secondary_carbon CCCC 2 124 363
8 C Secondary_carbon CCCC 2 124 363
9 C Primary_carbon, Secondary_carbon CCCC 2 124 363
10 C Primary_carbon, Secondary_carbon CCCC 2 124 363
12 C Secondary_carbon CCCC 3 124 363
13 C Secondary_carbon CCCC 3 124 363
14 C Primary_carbon, Secondary_carbon CCCC 3 124 363
15 C Primary_carbon, Secondary_carbon CCCC 3 124 363
17 C Secondary_carbon CCCC 4 124 363
18 C Secondary_carbon CCCC 4 124 363
19 C Primary_carbon, Secondary_carbon CCCC 4 124 363
20 C Primary_carbon, Secondary_carbon CCCC 4 124 363
0 C Primary_carbon, Secondary_carbon CCCCC 1 125 496
1 C Primary_carbon, Secondary_carbon CCCCC 1 125 496
2 C Secondary_carbon CCCCC 1 125 496
3 C Secondary_carbon CCCCC 1 125 496
4 C Secondary_carbon, Carboxylic_ester CCCCC 1 125 496
17 C Secondary_carbon, Carboxylic_ester CCCCC 2 125 496
18 C Secondary_carbon CCCCC 2 125 496
19 C Secondary_carbon CCCCC 2 125 496
20 C Primary_carbon, Secondary_carbon CCCCC 2 125 496
21 C Primary_carbon, Secondary_carbon CCCCC 2 125 496
23 O Ketone O 1 126 409
0 C Primary_carbon CC=O 1 128 147
1 C Primary_carbon CC=O 1 128 147
2 O NA CC=O 1 128 147
0 C Primary_carbon C 1 130 131
7 C Primary_carbon C 2 130 131
11 S NA CCS 1 133 137
12 C Primary_carbon CCS 1 133 137
13 C Primary_carbon CCS 1 133 137
6 C Primary_carbon C 1 134 202
9 C Isothiourea, Iminoarene, Aromatic, Conjugated_double_bond Cn1ccsc1 2 134 202
10 N Isothiourea, Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond Cn1ccsc1 2 134 202
11 C NA Cn1ccsc1 2 134 202
12 C Aromatic, Conjugated_double_bond Cn1ccsc1 2 134 202
13 C Aromatic, Conjugated_double_bond Cn1ccsc1 2 134 202
14 S Isothiourea, Hetero_S, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond Cn1ccsc1 2 134 202
2 C Secondary_carbon, Tertiary_carbon C1CC1 1 135 148
3 C Secondary_carbon, Tertiary_carbon C1CC1 1 135 148
4 C Secondary_carbon, Tertiary_carbon C1CC1 1 135 148
19 O Tertiary_alcohol O 2 135 148
0 C Primary_carbon C 1 138 238
22 N Secondary_amide CN 2 138 238
23 C Secondary_amide CN 2 138 238
0 C Primary_carbon C 1 139 265
4 S NA S 2 139 265
7 C Primary_carbon C 3 139 265
11 S Dialkylthioether CCS 4 139 265
12 C Primary_carbon, Dialkylthioether CCS 4 139 265
13 C Primary_carbon CCS 4 139 265
5 N Phosphoric_diestermonoamide CC(C)N 1 140 209
6 C Primary_carbon CC(C)N 1 140 209
7 C Primary_carbon CC(C)N 1 140 209
8 C Primary_carbon CC(C)N 1 140 209
15 C Primary_carbon C 2 140 209
17 S Alkylarylthioether CS 3 140 209
18 C Alkylarylthioether CS 3 140 209
0 C Primary_carbon, Secondary_carbon CC 1 143 147
1 C Primary_carbon, Secondary_carbon CC 1 143 147
3 C Primary_carbon C 2 143 147
7 N Heterocyclic O=C1NCCS1 3 143 147
8 C NA O=C1NCCS1 3 143 147
9 C NA O=C1NCCS1 3 143 147
10 S Heterocyclic O=C1NCCS1 3 143 147
11 C NA O=C1NCCS1 3 143 147
12 O NA O=C1NCCS1 3 143 147
15 C Primary_carbon C 4 143 147
0 C Primary_carbon CCC 1 144 236
1 C Primary_carbon CCC 1 144 236
2 C Primary_carbon CCC 1 144 236
0 C Primary_carbon CCC 1 145 1016
1 C Primary_carbon, Carboxylic_ester CCC 1 145 1016
2 C Primary_carbon CCC 1 145 1016
5 O Carboxylic_ester, Conjugated_double_bond O 2 145 1016
7 C Ketenacetal, Conjugated_double_bond C1CSCS1 3 145 1016
8 S Ketenacetal, Heterocyclic C1CSCS1 3 145 1016
9 C NA C1CSCS1 3 145 1016
10 C NA C1CSCS1 3 145 1016
11 S Ketenacetal, Heterocyclic C1CSCS1 3 145 1016
15 C Primary_carbon, Carboxylic_ester CCC 4 145 1016
16 C Primary_carbon CCC 4 145 1016
17 C Primary_carbon CCC 4 145 1016
10 C Secondary_carbon CCC 1 146 170
11 C Secondary_carbon CCC 1 146 170
12 C Secondary_carbon CCC 1 146 170
16 O Urea, Oxoarene, Conjugated_double_bond O 2 146 170
4 N NA N 1 147 167
5 C Quaternary_carbon, Nitrile C#N 1 148 172
6 N Nitrile C#N 1 148 172
0 C Primary_carbon, Secondary_carbon CCC 1 150 230
1 C Primary_carbon, Secondary_carbon CCC 1 150 230
2 C Secondary_carbon CCC 1 150 230
5 O Lactam, Oxoarene, Conjugated_double_bond O 2 150 230
7 C Aromatic, Conjugated_double_bond ccc(c)I 3 150 230
8 C Aryliodide, Aromatic ccc(c)I 3 150 230
9 C Aromatic ccc(c)I 3 150 230
10 C Aromatic ccc(c)I 3 150 230
14 O Alkylarylether, Isourea CCCO 4 150 230
15 C Secondary_carbon, Alkylarylether CCCO 4 150 230
16 C Primary_carbon, Secondary_carbon CCCO 4 150 230
17 C Primary_carbon, Secondary_carbon CCCO 4 150 230
18 I Aryliodide ccc(c)I 3 150 230
3 O NA O 1 154 203
11 C Aromatic cc(Cl)cn 2 154 203
12 C Arylchloride, Aromatic cc(Cl)cn 2 154 203
13 C Aromatic cc(Cl)cn 2 154 203
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cc(Cl)cn 2 154 203
15 Cl Arylchloride cc(Cl)cn 2 154 203
0 C Primary_carbon C 1 155 552
6 C Primary_carbon C 2 155 552
10 C Primary_carbon C 3 155 552
11 C Carboxylic_ester COC=O 4 155 552
12 O Carboxylic_ester COC=O 4 155 552
13 O Carboxylic_ester COC=O 4 155 552
14 C Carboxylic_ester COC=O 4 155 552
6 Cl Arylchloride Cl 1 157 456
7 Cl Arylchloride Cl 2 157 456
13 Br Alkylbromide Br 3 157 456
15 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 4 157 456
16 C Aromatic c1ncnn1 4 157 456
17 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 4 157 456
18 C Aromatic c1ncnn1 4 157 456
19 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 4 157 456
0 C Primary_carbon, Secondary_carbon CCC 1 158 206
1 C Primary_carbon, Secondary_carbon CCC 1 158 206
2 C Secondary_carbon CCC 1 158 206
11 C Primary_carbon C 2 158 206
15 S Sulfuric_esteramide CN(C)[SH](=O)=O 3 158 206
16 O Sulfuric_esteramide CN(C)[SH](=O)=O 3 158 206
17 O Sulfuric_esteramide CN(C)[SH](=O)=O 3 158 206
18 N Sulfuric_esteramide CN(C)[SH](=O)=O 3 158 206
19 C Sulfuric_esteramide CN(C)[SH](=O)=O 3 158 206
20 C Sulfuric_esteramide CN(C)[SH](=O)=O 3 158 206
0 C Primary_carbon C 1 162 207
7 C Primary_carbon C 2 162 207
15 C Primary_carbon, Tertiary_carbon CCC 3 162 207
16 C Primary_carbon, Tertiary_carbon CCC 3 162 207
17 C Primary_carbon, Tertiary_carbon CCC 3 162 207
9 Cl Chloroalkene Cl 1 163 197
10 Cl Chloroalkene Cl 2 163 197
13 Cl Arylchloride Cl 1 164 181
0 C Primary_carbon, Secondary_carbon C 1 167 265
8 C Primary_carbon C 2 167 265
9 S NA CCCS 3 167 265
10 C Secondary_carbon CCCS 3 167 265
11 C Primary_carbon, Secondary_carbon CCCS 3 167 265
12 C Primary_carbon, Secondary_carbon CCCS 3 167 265
13 Cl Arylchloride Cl 1 168 243
14 C Aromatic c1cncnc1 2 168 243
15 C Aromatic c1cncnc1 2 168 243
16 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1cncnc1 2 168 243
17 C Aromatic c1cncnc1 2 168 243
18 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1cncnc1 2 168 243
19 C Aromatic c1cncnc1 2 168 243
20 O Tertiary_alcohol O 3 168 243
21 Cl Arylchloride Cl 4 168 243
0 C Aromatic c1ccccc1 1 169 177
1 C Aromatic c1ccccc1 1 169 177
2 C Aromatic c1ccccc1 1 169 177
3 C Quaternary_carbon, Aromatic c1ccccc1 1 169 177
4 C Aromatic c1ccccc1 1 169 177
5 C Aromatic c1ccccc1 1 169 177
17 N Nitrile N 2 169 177
6 Cl Arylchloride Cl 1 170 659
7 Cl Arylchloride Cl 2 170 659
19 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 3 170 659
20 C Aromatic c1ncnn1 3 170 659
21 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 3 170 659
22 C Aromatic c1ncnn1 3 170 659
23 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 3 170 659
24 F Arylfluoride F 4 170 659
0 C Primary_carbon, Secondary_carbon C 1 172 201
19 O Tertiary_alcohol O 2 172 201
0 C Alkene C=CCO 1 173 311
1 C Alkene C=CCO 1 173 311
2 C Dialkylether C=CCO 1 173 311
3 O Dialkylether C=CCO 1 173 311
6 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1cncn1 2 173 311
7 C Aromatic c1cncn1 2 173 311
8 C Aromatic c1cncn1 2 173 311
9 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1cncn1 2 173 311
10 C Aromatic c1cncn1 2 173 311
17 Cl Arylchloride Cl 3 173 311
18 Cl Arylchloride Cl 4 173 311
0 C Primary_carbon, Tertiary_carbon C 1 174 175
2 C Primary_carbon, Tertiary_carbon C 2 174 175
0 C Primary_carbon, Secondary_carbon CCC 1 176 302
1 C Primary_carbon, Secondary_carbon CCC 1 176 302
2 C Secondary_carbon CCC 1 176 302
7 C NA Cn1cncn1 2 176 302
8 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 2 176 302
9 C Aromatic Cn1cncn1 2 176 302
10 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 2 176 302
11 C Aromatic Cn1cncn1 2 176 302
12 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 2 176 302
19 Cl Arylchloride Cl 3 176 302
20 Cl Arylchloride Cl 4 176 302
14 C NA Cn1cncn1 1 177 200
15 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 1 177 200
16 C Aromatic Cn1cncn1 1 177 200
17 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 1 177 200
18 C Aromatic Cn1cncn1 1 177 200
19 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 1 177 200
4 C Tertiary_carbon Cn1cncn1 1 178 589
5 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 1 178 589
6 C Aromatic Cn1cncn1 1 178 589
7 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 1 178 589
8 C Aromatic Cn1cncn1 1 178 589
9 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 1 178 589
12 C Alkylfluoride, Dialkylether, Halogen_acetal_like, Acetal_like FC(F)C(F)F 2 178 589
13 C Alkylfluoride FC(F)C(F)F 2 178 589
14 F Alkylfluoride FC(F)C(F)F 2 178 589
15 F Alkylfluoride FC(F)C(F)F 2 178 589
16 F Alkylfluoride, Halogen_acetal_like, Acetal_like FC(F)C(F)F 2 178 589
17 F Alkylfluoride, Halogen_acetal_like, Acetal_like FC(F)C(F)F 2 178 589
21 Cl Arylchloride Cl 3 178 589
22 Cl Arylchloride Cl 4 178 589
0 C Primary_carbon C 1 179 737
8 C Aromatic cnn 2 179 737
9 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cnn 2 179 737
10 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cnn 2 179 737
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 181 782
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 181 782
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 181 782
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 181 782
13 Cl Arylchloride Cl 2 181 782
14 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond c1ncnn1 3 181 782
15 C Aromatic, Conjugated_double_bond c1ncnn1 3 181 782
16 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 3 181 782
17 C Aromatic c1ncnn1 3 181 782
18 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond c1ncnn1 3 181 782
19 O Secondary_alcohol O 4 181 782
18 C Aromatic c1ccccc1 1 183 215
19 C Aromatic c1ccccc1 1 183 215
20 C Aromatic c1ccccc1 1 183 215
21 C Aromatic c1ccccc1 1 183 215
22 C Aromatic c1ccccc1 1 183 215
23 C Aromatic c1ccccc1 1 183 215
24 O Secondary_alcohol O 2 183 215
13 C Secondary_carbon, Tertiary_carbon CCSC(C)C 1 184 213
14 C Primary_carbon, Secondary_carbon, Dialkylthioether CCSC(C)C 1 184 213
15 C Primary_carbon CCSC(C)C 1 184 213
16 S Dialkylthioether CCSC(C)C 1 184 213
17 C Primary_carbon, Dialkylthioether CCSC(C)C 1 184 213
18 C Primary_carbon CCSC(C)C 1 184 213
0 C Primary_carbon, Quaternary_carbon C 1 186 639
16 Cl Arylchloride Cl 2 186 639
17 Cl Arylchloride Cl 3 186 639
18 O Phenol O 4 186 639
0 C Tertiary_amide CNC 1 187 247
1 N Tertiary_amide CNC 1 187 247
2 C Tertiary_amide CNC 1 187 247
24 O Alkylarylether, Imidolactone CO 2 187 247
25 C Alkylarylether, Imidolactone CO 2 187 247
26 O Alkylarylether, Imidolactone CO 3 187 247
27 C Alkylarylether, Imidolactone CO 3 187 247
28 N Secondary_amide NC=O 4 187 247
29 C Secondary_amide NC=O 4 187 247
30 O Secondary_amide NC=O 4 187 247
14 O NA O 1 189 190
0 C Primary_carbon CCO 1 190 222
1 C Primary_carbon, Carboxylic_ester CCO 1 190 222
2 O Carboxylic_ester CCO 1 190 222
4 O Carboxylic_ester O 2 190 222
8 O Carboxylic_ester O 3 190 222
9 O Carboxylic_ester CCO 4 190 222
10 C Primary_carbon, Carboxylic_ester CCO 4 190 222
11 C Primary_carbon CCO 4 190 222
13 P NA CO[PH](=S)OC 5 190 222
14 S NA CO[PH](=S)OC 5 190 222
15 O NA CO[PH](=S)OC 5 190 222
16 C NA CO[PH](=S)OC 5 190 222
17 O NA CO[PH](=S)OC 5 190 222
18 C NA CO[PH](=S)OC 5 190 222
0 C Primary_carbon CCO 1 191 265
1 C Primary_carbon, Urethan CCO 1 191 265
2 O Urethan CCO 1 191 265
4 O Urethan O 2 191 265
6 C NA C 3 191 265
12 S NA S 4 191 265
15 C Primary_carbon C 5 191 265
18 C Primary_carbon C 6 191 265
0 C Primary_carbon CC 1 192 269
1 C Primary_carbon, Alkyne, Conjugated_tripple_bond CC 1 192 269
12 O Carboxylic_ester O 1 193 196
18 O Dialkylether CO 2 193 196
19 C Dialkylether CO 2 193 196
10 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1cnnc1 1 194 196
11 C Aromatic c1cnnc1 1 194 196
12 C Aromatic c1cnnc1 1 194 196
13 C Aromatic c1cnnc1 1 194 196
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1cnnc1 1 194 196
0 C Primary_carbon, Secondary_carbon CC 1 196 202
1 C Primary_carbon, Secondary_carbon CC 1 196 202
7 C Primary_carbon C 2 196 202
13 O Dialkylether CO 3 196 202
14 C Dialkylether CO 3 196 202
15 C Tertiary_amide O=CCCl 4 196 202
16 O Tertiary_amide O=CCCl 4 196 202
17 C Alkylchloride O=CCCl 4 196 202
18 Cl Alkylchloride O=CCCl 4 196 202
0 C Primary_carbon C 1 197 294
9 O Phosphoric_triester O 2 197 294
0 C Primary_carbon CCS 1 198 521
1 C Primary_carbon CCS 1 198 521
2 S NA CCS 1 198 521
4 O NA O 2 198 521
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 200 329
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 200 329
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 200 329
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 200 329
13 Cl Arylchloride Cl 2 200 329
14 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 3 200 329
15 C Aromatic c1ncnn1 3 200 329
16 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 3 200 329
17 C Aromatic c1ncnn1 3 200 329
18 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 3 200 329
19 O Secondary_alcohol O 4 200 329
0 C Primary_carbon, Secondary_carbon CC 1 201 311
1 C Primary_carbon, Secondary_carbon CC 1 201 311
5 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 2 201 311
6 C Aromatic c1ncnn1 2 201 311
7 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 2 201 311
8 C Aromatic c1ncnn1 2 201 311
9 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 2 201 311
16 Cl Arylchloride Cl 3 201 311
17 Cl Arylchloride Cl 4 201 311
0 C Primary_carbon, Secondary_carbon CC 1 202 289
1 C Primary_carbon, Secondary_carbon CC 1 202 289
3 C Primary_carbon, Secondary_carbon CC 2 202 289
4 C Primary_carbon, Secondary_carbon CC 2 202 289
10 C Primary_carbon C 3 202 289
14 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 4 202 289
15 O Anion O=[NH+][O-] 4 202 289
16 O Conjugated_double_bond O=[NH+][O-] 4 202 289
17 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 5 202 289
18 O Anion O=[NH+][O-] 5 202 289
19 O Conjugated_double_bond O=[NH+][O-] 5 202 289
0 C Primary_carbon C 1 204 246
3 C Primary_carbon, Tertiary_amide CC 2 204 246
4 C Primary_carbon CC 2 204 246
17 Cl Chloroalkene Cl 3 204 246
9 C Urethan CN(C)C=O 1 206 230
10 O Urethan CN(C)C=O 1 206 230
11 N Urethan CN(C)C=O 1 206 230
12 C NA CN(C)C=O 1 206 230
13 C NA CN(C)C=O 1 206 230
16 C NA C 2 206 230
3 C Primary_carbon CC 1 207 230
4 C Primary_carbon CC 1 207 230
13 P NA CO[PH](=S)OC 2 207 230
14 S NA CO[PH](=S)OC 2 207 230
15 O NA CO[PH](=S)OC 2 207 230
16 C NA CO[PH](=S)OC 2 207 230
17 O NA CO[PH](=S)OC 2 207 230
18 C NA CO[PH](=S)OC 2 207 230
0 C Primary_carbon, Quaternary_carbon C 1 208 406
2 C Secondary_carbon, Quaternary_carbon C 2 208 406
4 C Primary_carbon, Quaternary_carbon C 3 208 406
14 Cl Arylchloride Cl 4 208 406
15 Cl Arylchloride Cl 5 208 406
0 C Primary_carbon, Secondary_carbon CCCS 1 209 236
1 C Primary_carbon, Secondary_carbon CCCS 1 209 236
2 C Secondary_carbon CCCS 1 209 236
3 S NA CCCS 1 209 236
5 O NA O 2 209 236
8 C Primary_carbon C 3 209 236
16 Cl Arylchloride Cl 4 209 236
17 Br Arylbromide Br 5 209 236
0 C Primary_carbon CCN 1 210 294
1 C Primary_carbon CCN 1 210 294
2 N NA CCN 1 210 294
14 C Primary_carbon C 2 210 294
15 C Primary_carbon C 3 210 294
16 C Primary_carbon C 4 210 294
8 S Halogen_acetal_like, Acetal_like FC(S)(Cl)Cl 1 214 731
9 C Alkylchloride, Alkylfluoride, Halogen_acetal_like, Acetal_like FC(S)(Cl)Cl 1 214 731
10 Cl Alkylchloride, Halogen_acetal_like, Acetal_like FC(S)(Cl)Cl 1 214 731
11 Cl Alkylchloride, Halogen_acetal_like, Acetal_like FC(S)(Cl)Cl 1 214 731
12 F Alkylfluoride, Halogen_acetal_like, Acetal_like FC(S)(Cl)Cl 1 214 731
16 N NA CNC 2 214 731
17 C NA CNC 2 214 731
18 C NA CNC 2 214 731
5 O Ketone O 1 215 273
0 C Primary_carbon CCO 1 220 258
1 C Primary_carbon, Carboxylic_ester CCO 1 220 258
2 O Carboxylic_ester CCO 1 220 258
4 O Carboxylic_ester O 2 220 258
10 C Primary_carbon C 3 220 258
0 C Primary_carbon, CH-acidic C 1 222 322
17 Cl Arylchloride Cl 1 225 245
0 C Primary_carbon C 1 227 531
9 Cl Imidoylhalide_cyclic, Arylchloride Cl 2 227 531
12 C Nitrile, Conjugated_tripple_bond C#N 3 227 531
13 N Nitrile, Conjugated_tripple_bond C#N 3 227 531
15 S Sulfuric_diamide, Conjugated_double_bond CN(C)[SH](=O)=O 4 227 531
16 O Sulfuric_diamide, Conjugated_double_bond CN(C)[SH](=O)=O 4 227 531
17 O Sulfuric_diamide, Conjugated_double_bond CN(C)[SH](=O)=O 4 227 531
18 N Sulfuric_diamide CN(C)[SH](=O)=O 4 227 531
19 C NA CN(C)[SH](=O)=O 4 227 531
20 C NA CN(C)[SH](=O)=O 4 227 531
0 C Primary_carbon CCN 1 228 336
1 C Primary_carbon CCN 1 228 336
2 N Urea CCN 1 228 336
4 O Urea O 2 228 336
12 C Nitrile, Conjugated_double_bond, Conjugated_tripple_bond C#N 3 228 336
13 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond C#N 3 228 336
6 O Tertiary_amide, Conjugated_double_bond O 1 229 482
12 C Primary_carbon C 2 229 482
0 C Primary_carbon, Secondary_carbon CCCC 1 230 356
1 C Primary_carbon, Secondary_carbon CCCC 1 230 356
2 C Secondary_carbon CCCC 1 230 356
3 C Secondary_carbon CCCC 1 230 356
6 C Primary_carbon C 2 230 356
9 N NA CCN 3 230 356
10 C Primary_carbon CCN 3 230 356
11 C Primary_carbon CCN 3 230 356
14 O Imidoacid_cyclic, Phenol O 4 230 356
0 C Primary_carbon CC(C)O 1 236 276
1 C Primary_carbon, Carboxylic_ester CC(C)O 1 236 276
2 C Primary_carbon CC(C)O 1 236 276
3 O Carboxylic_ester CC(C)O 1 236 276
5 O Carboxylic_ester, Conjugated_double_bond O 2 236 276
13 P NA CO[PH](N)=S 3 236 276
14 S NA CO[PH](N)=S 3 236 276
15 N NA CO[PH](N)=S 3 236 276
16 O NA CO[PH](N)=S 3 236 276
17 C NA CO[PH](N)=S 3 236 276
16 N Oximether, Conjugated_double_bond CON 1 238 934
17 O Oximether CON 1 238 934
18 C Oximether CON 1 238 934
19 C Carboxylic_ester, Conjugated_double_bond COC=O 2 238 934
20 O Carboxylic_ester, Conjugated_double_bond COC=O 2 238 934
21 O Carboxylic_ester COC=O 2 238 934
22 C Carboxylic_ester COC=O 2 238 934
11 Cl Arylchloride Cl 1 239 295
12 Cl Arylchloride Cl 2 239 295
0 C Alkyne C 1 240 425
12 O Secondary_amide O 2 240 425
20 Cl Arylchloride Cl 3 240 425
22 C Dialkylether C#CC 4 240 425
23 C Alkyne C#CC 4 240 425
24 C Alkyne C#CC 4 240 425
27 O Alkylarylether CO 5 240 425
28 C Alkylarylether CO 5 240 425
0 C Primary_carbon C 1 242 877
12 O Lactam, Oxoarene, Conjugated_double_bond O 2 242 877
14 N NA N 3 242 877
0 C Primary_carbon C 1 243 935
11 C Primary_carbon C 2 243 935
16 O Alkylarylether CO 3 243 935
17 C Alkylarylether CO 3 243 935
18 Br Arylbromide Br 4 243 935
21 O Alkylarylether CO 5 243 935
22 C Alkylarylether CO 5 243 935
24 C Alkylarylether C 6 243 935
17 C Carboxylic_ester, Conjugated_double_bond COC=O 1 245 256
18 O Carboxylic_ester, Conjugated_double_bond COC=O 1 245 256
19 O Carboxylic_ester COC=O 1 245 256
20 C Carboxylic_ester COC=O 1 245 256
0 C Primary_carbon C 1 246 294
5 N Secondary_amide CN 2 246 294
6 C Secondary_amide CN 2 246 294
9 O Phosphoric_triester O 3 246 294
0 C Primary_carbon C 1 247 264
4 C Primary_carbon C 2 247 264
24 C Carboxylic_ester C1COC1 3 247 264
25 C Dialkylether C1COC1 3 247 264
26 O Dialkylether, Heterocyclic C1COC1 3 247 264
27 C Dialkylether C1COC1 3 247 264
0 C Primary_carbon C 1 248 284
10 C Primary_carbon C 1 250 316
12 N Primary_aliph_amine, Enamine N 1 253 851
13 Cl Chloroalkene Cl 2 253 851
10 C Aromatic cccc 1 257 268
11 C Aromatic cccc 1 257 268
12 C Aromatic cccc 1 257 268
13 C Aromatic cccc 1 257 268
0 C Primary_carbon, Secondary_carbon CCC 1 258 263
1 C Primary_carbon, Secondary_carbon CCC 1 258 263
2 C Secondary_carbon CCC 1 258 263
6 C Secondary_carbon CCC 2 258 263
7 C Primary_carbon, Secondary_carbon CCC 2 258 263
8 C Primary_carbon, Secondary_carbon CCC 2 258 263
0 C Primary_carbon CCO 1 259 289
1 C Primary_carbon, Alkylarylether CCO 1 259 289
2 O Alkylarylether CCO 1 259 289
9 O Alkylarylether CCO 2 259 289
10 C Primary_carbon, Alkylarylether CCO 2 259 289
11 C Primary_carbon CCO 2 259 289
15 O Urethan CC(C)O 3 259 289
16 C Primary_carbon, Urethan CC(C)O 3 259 289
17 C Primary_carbon CC(C)O 3 259 289
18 C Primary_carbon CC(C)O 3 259 289
6 C Alkylfluoride, Trifluoromethyl FC(F)F 1 261 320
7 F Alkylfluoride, Trifluoromethyl FC(F)F 1 261 320
8 F Alkylfluoride, Trifluoromethyl FC(F)F 1 261 320
9 F Alkylfluoride, Trifluoromethyl FC(F)F 1 261 320
11 O Secondary_amide, Conjugated_double_bond O 2 261 320
15 N Nitrile N 3 261 320
7 O NA O 1 265 285
17 Cl Arylchloride Cl 1 266 319
18 C Secondary_carbon C1CCCC1 2 266 319
19 C Secondary_carbon C1CCCC1 2 266 319
20 C Secondary_carbon C1CCCC1 2 266 319
21 C Secondary_carbon C1CCCC1 2 266 319
22 C Secondary_carbon C1CCCC1 2 266 319
0 C Primary_carbon C 1 268 1004
2 C Primary_carbon C 2 268 1004
12 O Urethan O 3 268 1004
13 N Urethan CN 4 268 1004
14 C NA CN 4 268 1004
4 C Primary_carbon C 1 269 283
0 C Primary_carbon, Quaternary_carbon C 1 273 393
2 C Primary_carbon, Quaternary_carbon C 2 273 393
3 C Primary_carbon, Quaternary_carbon C 3 273 393
6 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 4 273 393
7 C Aromatic c1ncnn1 4 273 393
8 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 4 273 393
9 C Aromatic c1ncnn1 4 273 393
10 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 4 273 393
18 Cl Arylchloride Cl 5 273 393
3 O Phosphonic_diester O 1 274 285
4 C NA OCC(Cl)(Cl)Cl 2 274 285
5 C Alkylchloride OCC(Cl)(Cl)Cl 2 274 285
6 Cl Alkylchloride OCC(Cl)(Cl)Cl 2 274 285
7 Cl Alkylchloride OCC(Cl)(Cl)Cl 2 274 285
8 Cl Alkylchloride OCC(Cl)(Cl)Cl 2 274 285
9 O NA OCC(Cl)(Cl)Cl 2 274 285
6 Cl Arylchloride Cl 1 275 316
13 C Primary_carbon CC 2 275 316
14 C Primary_carbon CC 2 275 316
6 C Primary_carbon C 1 276 311
0 C Primary_carbon, Secondary_carbon C 1 277 482
3 C Primary_carbon C 2 277 482
4 C Ketone O=CCCl 3 277 482
5 O Ketone O=CCCl 3 277 482
6 C Alkylchloride, Ketone O=CCCl 3 277 482
7 Cl Alkylchloride O=CCCl 3 277 482
10 O Secondary_amide, Conjugated_double_bond O 4 277 482
15 C Primary_carbon C 5 277 482
18 Cl Arylchloride Cl 6 277 482
19 Cl Arylchloride Cl 7 277 482
0 C Primary_carbon CC(C)(C)O 1 280 302
1 C Primary_carbon, Secondary_carbon, Alkylarylether CC(C)(C)O 1 280 302
2 C Primary_carbon CC(C)(C)O 1 280 302
3 C Secondary_carbon CC(C)(C)O 1 280 302
10 O Alkylarylether, Heterocyclic CC(C)(C)O 1 280 302
0 C Primary_carbon CCOC(N)=O 1 284 302
1 C Primary_carbon, Urethan CCOC(N)=O 1 284 302
2 O Urethan CCOC(N)=O 1 284 302
3 C Urethan CCOC(N)=O 1 284 302
4 O Urethan CCOC(N)=O 1 284 302
5 N Urethan CCOC(N)=O 1 284 302
16 C Aromatic c1ccccc1 2 284 302
17 C Aromatic c1ccccc1 2 284 302
18 C Aromatic c1ccccc1 2 284 302
19 C Aromatic c1ccccc1 2 284 302
20 C Aromatic c1ccccc1 2 284 302
21 C Aromatic c1ccccc1 2 284 302
0 C Secondary_amide CNC(=O)CS 1 285 294
1 N Secondary_amide CNC(=O)CS 1 285 294
2 C Secondary_amide CNC(=O)CS 1 285 294
3 O Secondary_amide CNC(=O)CS 1 285 294
4 C NA CNC(=O)CS 1 285 294
5 S NA CNC(=O)CS 1 285 294
0 C Primary_carbon CC 1 286 372
1 C Primary_carbon, CH-acidic CC 1 286 372
10 C NA C 2 286 372
13 N Urea CN 3 286 372
14 C NA CN 3 286 372
2 C NA C 1 289 295
12 C Alkylfluoride, Trifluoromethyl FC(F)F 2 289 295
13 F Alkylfluoride, Trifluoromethyl FC(F)F 2 289 295
14 F Alkylfluoride, Trifluoromethyl FC(F)F 2 289 295
15 F Alkylfluoride, Trifluoromethyl FC(F)F 2 289 295
7 C NA Cn1cncn1 1 291 530
8 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 1 291 530
9 C Aromatic Cn1cncn1 1 291 530
10 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 1 291 530
11 C Aromatic Cn1cncn1 1 291 530
12 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cn1cncn1 1 291 530
19 F Arylfluoride F 2 291 530
21 F Arylfluoride F 3 291 530
22 Cl Arylchloride Cl 1 292 335
11 Br Arylbromide Br 1 295 298
12 O NA CO 2 295 298
13 C NA CO 2 295 298
0 C Primary_carbon CCON 1 296 515
1 C Primary_carbon CCON 1 296 515
2 O NA CCON 1 296 515
3 N Conjugated_double_bond CCON 1 296 515
11 O Alkylarylether CO 2 296 515
12 C Alkylarylether CO 2 296 515
13 Cl Arylchloride Cl 3 296 515
14 O Alkylarylether CO 4 296 515
15 C Alkylarylether CO 4 296 515
18 O Conjugated_double_bond O 5 296 515
19 C Aromatic, Conjugated_double_bond c1ccccc1 6 296 515
20 C Aromatic, Conjugated_double_bond c1ccccc1 6 296 515
21 C Aromatic c1ccccc1 6 296 515
22 C Aromatic c1ccccc1 6 296 515
23 C Aromatic c1ccccc1 6 296 515
24 C Aromatic, Conjugated_double_bond c1ccccc1 6 296 515
0 C Primary_carbon C 1 298 303
7 Cl Arylchloride Cl 2 298 303
0 C NA CN(C)C(N)=O 1 299 411
1 N Urea CN(C)C(N)=O 1 299 411
2 C NA CN(C)C(N)=O 1 299 411
3 C Urea CN(C)C(N)=O 1 299 411
4 O Urea CN(C)C(N)=O 1 299 411
5 N Urea CN(C)C(N)=O 1 299 411
19 Cl Arylchloride Cl 2 299 411
0 C NA CN(C)C=O 1 300 350
1 N Urea CN(C)C=O 1 300 350
2 C NA CN(C)C=O 1 300 350
3 C Urea CN(C)C=O 1 300 350
4 O Urea CN(C)C=O 1 300 350
3 N Guanidine, Nitro, Conjugated_double_bond N[N+](=O)[O-] 1 301 303
4 N Nitro, Conjugated_double_bond, Kation N[N+](=O)[O-] 1 301 303
5 O Anion N[N+](=O)[O-] 1 301 303
6 O Conjugated_double_bond N[N+](=O)[O-] 1 301 303
8 C Tertiary_carbon CC1CCOC1 2 301 303
9 C Secondary_carbon, Tertiary_carbon CC1CCOC1 2 301 303
10 C Secondary_carbon, Tertiary_carbon CC1CCOC1 2 301 303
11 C Secondary_carbon, Dialkylether CC1CCOC1 2 301 303
12 O Dialkylether, Heterocyclic CC1CCOC1 2 301 303
13 C Tertiary_carbon, Dialkylether CC1CCOC1 2 301 303
11 C Acetal, Acetal_like C1COCO1 1 302 307
12 O Acetal, Acetal_like, Heterocyclic C1COCO1 1 302 307
13 C Acetal C1COCO1 1 302 307
14 C Acetal C1COCO1 1 302 307
15 O Acetal, Acetal_like, Heterocyclic C1COCO1 1 302 307
0 C Aromatic c1ccccc1 1 304 722
1 C Aromatic c1ccccc1 1 304 722
2 C Aromatic c1ccccc1 1 304 722
3 C Aromatic c1ccccc1 1 304 722
4 C Aromatic c1ccccc1 1 304 722
5 C Aromatic c1ccccc1 1 304 722
8 O Urea O 2 304 722
16 Cl Imidoylhalide_cyclic, Arylchloride Cl 3 304 722
10 C Primary_carbon C 1 305 309
11 C Carboxylic_ester COC=O 2 305 309
12 O Carboxylic_ester COC=O 2 305 309
13 O Carboxylic_ester COC=O 2 305 309
14 C Carboxylic_ester COC=O 2 305 309
16 O Tertiary_amide, Conjugated_double_bond O 3 305 309
17 C Aromatic, Conjugated_double_bond c1ccoc1 4 305 309
18 C Aromatic, Conjugated_double_bond c1ccoc1 4 305 309
19 C Aromatic c1ccoc1 4 305 309
20 C Aromatic c1ccoc1 4 305 309
21 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond c1ccoc1 4 305 309
8 S Alkylarylthioether CS 1 307 311
9 C Alkylarylthioether CS 1 307 311
2 C Primary_carbon C 1 308 316
11 O Dialkylether CO 2 308 316
12 C Dialkylether CO 2 308 316
16 S Alkylarylthioether CS 3 308 316
17 C Alkylarylthioether CS 3 308 316
8 N Tertiary_mixed_amine CNC 1 309 311
9 C NA CNC 1 309 311
10 C NA CNC 1 309 311
12 C Nitro, Conjugated_double_bond C[N+](=O)[O-] 1 310 320
13 N Nitro, Conjugated_double_bond, Kation C[N+](=O)[O-] 1 310 320
14 O Anion C[N+](=O)[O-] 1 310 320
15 O Conjugated_double_bond C[N+](=O)[O-] 1 310 320
16 N NA CN 2 310 320
17 C NA CN 2 310 320
0 C Primary_carbon, Tertiary_carbon CCC 1 311 815
1 C Primary_carbon, Tertiary_carbon CCC 1 311 815
2 C Primary_carbon, Tertiary_carbon CCC 1 311 815
6 C Primary_carbon C 2 311 815
12 O Urethan O 3 311 815
13 N Urethan CN 4 311 815
14 C NA CN 4 311 815
0 C Primary_carbon C 1 314 378
11 C Carboxylic_acid, Conjugated_double_bond O=CO 2 314 378
12 O Carboxylic_acid, Conjugated_double_bond O=CO 2 314 378
13 O Carboxylic_acid O=CO 2 314 378
14 Cl Arylchloride Cl 3 314 378
0 C Alkene C 1 315 947
0 C Primary_carbon, Secondary_carbon CC 1 316 386
1 C Primary_carbon, Secondary_carbon CC 1 316 386
3 C Primary_carbon C 2 316 386
10 C Primary_carbon C 3 316 386
14 O Alkylarylether CO 4 316 386
15 C Alkylarylether CO 4 316 386
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 317 372
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 317 372
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 317 372
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 317 372
9 C NA C 2 317 372
12 N Urea CN 3 317 372
13 C NA CN 3 317 372
10 C Aromatic c1csnn1 1 318 326
11 C Aromatic c1csnn1 1 318 326
12 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1csnn1 1 318 326
13 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1csnn1 1 318 326
14 S Hetero_S, Heteroaromatic, Aromatic, Heterocyclic c1csnn1 1 318 326
0 C Primary_carbon C 1 322 334
2 C Primary_carbon C 2 322 334
10 S Dialkylthioether CS 3 322 334
11 C Dialkylthioether CS 3 322 334
0 C Urethan COC(N)=O 1 323 343
1 O Urethan COC(N)=O 1 323 343
2 C Urethan COC(N)=O 1 323 343
3 O Urethan COC(N)=O 1 323 343
4 N Urethan COC(N)=O 1 323 343
8 O Alkylarylether CO 1 325 794
9 C Alkylarylether CO 1 325 794
13 O Tertiary_amide, Conjugated_double_bond O 2 325 794
14 N Tertiary_amide, Heterocyclic C1COCCN1 3 325 794
15 C Tertiary_amide C1COCCN1 3 325 794
16 C Dialkylether C1COCCN1 3 325 794
17 O Dialkylether, Heterocyclic C1COCCN1 3 325 794
18 C Dialkylether C1COCCN1 3 325 794
19 C Tertiary_amide C1COCCN1 3 325 794
26 Cl Arylchloride Cl 4 325 794
2 C NA C 1 326 510
4 O Urea O 2 326 510
13 Cl Arylchloride Cl 3 326 510
0 C Primary_carbon, Secondary_carbon C 1 329 969
3 C Primary_carbon, Tertiary_carbon C 2 329 969
12 O Urethan O 3 329 969
13 N Urethan CN 4 329 969
14 C NA CN 4 329 969
9 C Primary_carbon, Quaternary_carbon CC(C)C 1 330 348
10 C Primary_carbon, Quaternary_carbon CC(C)C 1 330 348
11 C Primary_carbon, Quaternary_carbon CC(C)C 1 330 348
12 C Primary_carbon, Quaternary_carbon CC(C)C 1 330 348
14 N Tertiary_aliph_amine, Heterocyclic C1CCNCC1 2 330 348
15 C Secondary_carbon C1CCNCC1 2 330 348
16 C Secondary_carbon C1CCNCC1 2 330 348
17 C Secondary_carbon C1CCNCC1 2 330 348
18 C Secondary_carbon C1CCNCC1 2 330 348
19 C Secondary_carbon C1CCNCC1 2 330 348
0 C Primary_carbon, Tertiary_carbon CCC 1 332 351
1 C Primary_carbon, Tertiary_carbon CCC 1 332 351
2 C Primary_carbon, Tertiary_carbon CCC 1 332 351
5 O Secondary_amide O 2 332 351
8 C Primary_carbon C 3 332 351
13 C Primary_carbon C 4 332 351
18 O Urethan O 5 332 351
19 O Urethan CC(C)O 6 332 351
20 C Primary_carbon, Urethan CC(C)O 6 332 351
21 C Primary_carbon CC(C)O 6 332 351
22 C Primary_carbon CC(C)O 6 332 351
0 C NA CNC=O 1 333 737
1 N Urea CNC=O 1 333 737
2 C Urea CNC=O 1 333 737
3 O Urea CNC=O 1 333 737
5 C NA C 2 333 737
24 C Primary_carbon C 1 335 342
25 O Alkylarylether CO 2 335 342
26 C Alkylarylether CO 2 335 342
8 O Tertiary_amide, Conjugated_double_bond O 1 336 347
9 N Tertiary_amide CNC 2 336 347
10 C Tertiary_amide CNC 2 336 347
11 C Tertiary_amide CNC 2 336 347
12 S NA CS 3 336 347
13 C NA CS 3 336 347
0 C Primary_carbon, Secondary_carbon CCCO 1 338 410
1 C Primary_carbon, Secondary_carbon CCCO 1 338 410
2 C Secondary_carbon, Urethan CCCO 1 338 410
3 O Urethan CCCO 1 338 410
7 C Secondary_carbon CCCN(C)C 2 338 410
8 C Secondary_carbon CCCN(C)C 2 338 410
9 C Secondary_carbon CCCN(C)C 2 338 410
10 N Tertiary_aliph_amine CCCN(C)C 2 338 410
11 C NA CCCN(C)C 2 338 410
12 C NA CCCN(C)C 2 338 410
0 C Aromatic cccc 1 343 463
1 C Aromatic cccc 1 343 463
2 C Aromatic cccc 1 343 463
5 C Aromatic cccc 1 343 463
8 C Aromatic c1cscn1 2 343 463
9 C Aromatic c1cscn1 2 343 463
10 S Hetero_S, Heteroaromatic, Aromatic, Heterocyclic c1cscn1 2 343 463
11 C Aromatic c1cscn1 2 343 463
12 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1cscn1 2 343 463
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 347 376
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 347 376
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 347 376
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 347 376
5 N NA CNC(=O)ON 2 347 376
6 O NA CNC(=O)ON 2 347 376
7 C NA CNC(=O)ON 2 347 376
8 O NA CNC(=O)ON 2 347 376
9 N NA CNC(=O)ON 2 347 376
10 C NA CNC(=O)ON 2 347 376
0 C Alkylarylether CO 1 349 597
1 O Alkylarylether CO 1 349 597
2 C Secondary_carbon, Tertiary_carbon CC(C)C 1 350 380
3 C Secondary_carbon, Tertiary_carbon, Bridged_rings CC(C)C 1 350 380
4 C Secondary_carbon, Tertiary_carbon CC(C)C 1 350 380
9 C Secondary_carbon, Tertiary_carbon CC(C)C 1 350 380
17 C Primary_carbon, Secondary_amide CC=O 1 351 702
18 O Secondary_amide CC=O 1 351 702
19 C Primary_carbon CC=O 1 351 702
0 C Aromatic c1ccccc1 1 353 585
1 C Aromatic c1ccccc1 1 353 585
2 C Aromatic c1ccccc1 1 353 585
3 C Aromatic c1ccccc1 1 353 585
4 C Aromatic c1ccccc1 1 353 585
5 C Aromatic c1ccccc1 1 353 585
13 N Primary_arom_amine N 1 354 660
19 N Primary_aliph_amine N 1 355 383
0 C NA C 1 356 532
0 C Primary_carbon C 1 357 522
11 N Azide [N-]=[N+]=N 2 357 522
12 N Azide, Kation [N-]=[N+]=N 2 357 522
13 N Azide, Anion [N-]=[N+]=N 2 357 522
18 O Lactam, Oxoarene, Conjugated_double_bond O 3 357 522
14 Br Arylbromide Br 1 359 879
0 C Secondary_carbon C1CNC1 1 361 410
1 C Secondary_carbon C1CNC1 1 361 410
2 N Secondary_aliph_amine, Alpha_aminoacid, Heterocyclic C1CNC1 1 361 410
3 C Secondary_carbon, Alpha_aminoacid C1CNC1 1 361 410
6 O Carboxylic_acid, Alpha_aminoacid O 2 361 410
0 C Primary_carbon C 1 363 376
7 O Carboxylic_ester CC(=O)O 2 363 376
8 C Primary_carbon, Carboxylic_ester CC(=O)O 2 363 376
9 O Carboxylic_ester CC(=O)O 2 363 376
10 C Primary_carbon, CH-acidic CC(=O)O 2 363 376
13 N Primary_arom_amine N 1 368 460
14 N Primary_arom_amine N 1 370 701
0 C Aromatic ccc 1 378 963
1 C Aromatic ccc 1 378 963
9 C Aromatic, Conjugated_double_bond ccc 1 378 963
11 O Imide_acidic, Conjugated_double_bond O 2 378 963
14 O Imide_acidic, Conjugated_double_bond O 3 378 963
15 N Primary_arom_amine N 4 378 963
9 O Oxoarene, Conjugated_double_bond O 1 379 437
7 N Amidine, Conjugated_double_bond N 1 380 410
9 N Primary_arom_amine N 2 380 410
6 F Arylfluoride F 1 381 519
9 C Carboxylic_acid, Conjugated_double_bond O=CO 2 381 519
10 O Carboxylic_acid, Conjugated_double_bond O=CO 2 381 519
11 O Carboxylic_acid O=CO 2 381 519
0 C Secondary_carbon CCCCN 1 383 652
1 C Secondary_carbon CCCCN 1 383 652
14 C Aromatic ccccCl 2 383 652
15 C Aromatic ccccCl 2 383 652
16 C Aromatic ccccCl 2 383 652
17 C Arylchloride, Aromatic ccccCl 2 383 652
18 Cl Arylchloride ccccCl 2 383 652
19 C Secondary_carbon CCCCN 1 383 652
20 C Secondary_carbon CCCCN 1 383 652
21 N Primary_aliph_amine CCCCN 1 383 652
10 S Sulfonic_acid O=[SH](=O)O 1 385 412
11 O Sulfonic_acid O=[SH](=O)O 1 385 412
12 O Sulfonic_acid O=[SH](=O)O 1 385 412
13 O Sulfonic_acid O=[SH](=O)O 1 385 412
14 O Tertiary_alcohol, 1,2-Aminoalcohol O 2 385 412
0 C Phosphoric_diester COP(=O)(O)O 1 387 394
17 O Phosphoric_diester, Heterocyclic COP(=O)(O)O 1 387 394
18 P Phosphoric_diester, Heterocyclic COP(=O)(O)O 1 387 394
19 O Phosphoric_diester COP(=O)(O)O 1 387 394
20 O Phosphoric_diester COP(=O)(O)O 1 387 394
21 O Phosphoric_diester, Heterocyclic COP(=O)(O)O 1 387 394
2 C Secondary_carbon CCN=C(N)S 1 388 400
3 C Secondary_carbon CCN=C(N)S 1 388 400
4 N Isothiourea, Heterocyclic CCN=C(N)S 1 388 400
5 C Isothiourea CCN=C(N)S 1 388 400
6 N Isothiourea CCN=C(N)S 1 388 400
7 S Isothiourea, Heterocyclic CCN=C(N)S 1 388 400
0 C Alkene C=C 1 389 399
1 C Alkene C=C 1 389 399
21 C NA C 2 389 399
0 C Primary_carbon, Ketone, CH-acidic CC=O 1 390 442
1 C Primary_carbon, Ketone, Conjugated_double_bond CC=O 1 390 442
2 O Ketone, Conjugated_double_bond CC=O 1 390 442
16 C Secondary_carbon C1CCCCC1 2 390 442
17 C Secondary_carbon C1CCCCC1 2 390 442
18 C Secondary_carbon C1CCCCC1 2 390 442
19 C Secondary_carbon C1CCCCC1 2 390 442
20 C Secondary_carbon C1CCCCC1 2 390 442
21 C Secondary_carbon C1CCCCC1 2 390 442
3 C Aromatic c1ccccc1 1 391 807
4 C Aromatic c1ccccc1 1 391 807
5 C Aromatic c1ccccc1 1 391 807
6 C Aromatic c1ccccc1 1 391 807
7 C Aromatic c1ccccc1 1 391 807
8 C Aromatic c1ccccc1 1 391 807
11 O Secondary_amide, Conjugated_double_bond O 2 391 807
14 C Primary_carbon C 3 391 807
16 C Aromatic c1ccccc1 4 391 807
17 C Aromatic c1ccccc1 4 391 807
18 C Aromatic c1ccccc1 4 391 807
19 C Aromatic c1ccccc1 4 391 807
20 C Aromatic c1ccccc1 4 391 807
21 C Aromatic c1ccccc1 4 391 807
24 C Aromatic cccc 5 391 807
25 C Aromatic cccc 5 391 807
26 C Aromatic cccc 5 391 807
27 C Aromatic cccc 5 391 807
7 C Carboxylic_acid, Alpha_aminoacid O=CO 1 392 797
8 O Carboxylic_acid, Alpha_aminoacid O=CO 1 392 797
9 O Carboxylic_acid, Alpha_aminoacid O=CO 1 392 797
13 C Carboxylic_acid, Conjugated_double_bond O=CO 2 392 797
14 O Carboxylic_acid, Conjugated_double_bond O=CO 2 392 797
15 O Carboxylic_acid O=CO 2 392 797
16 O Primary_amide O 1 393 903
17 N Primary_amide N 2 393 903
0 C Primary_carbon, Secondary_carbon CC 1 395 703
1 C Primary_carbon, Secondary_carbon, Quaternary_carbon CC 1 395 703
6 O Imide_acidic O 2 395 703
9 O Imide_acidic O 3 395 703
16 N Primary_arom_amine N 4 395 703
23 N Primary_arom_amine N 1 396 424
12 C Secondary_carbon, Tertiary_carbon CC(C)C 1 397 437
13 C Secondary_carbon, Tertiary_carbon, Bridged_rings CC(C)C 1 397 437
14 C Secondary_carbon, Tertiary_carbon CC(C)C 1 397 437
15 C Secondary_carbon, Tertiary_carbon, Quaternary_carbon CC(C)C 1 397 437
19 C NA CN 2 397 437
20 N Primary_aliph_amine CN 2 397 437
22 O Phenol, 1,2-Diphenol O 3 397 437
7 C Secondary_carbon CN 1 398 410
8 N Primary_aliph_amine CN 1 398 410
9 S Sulfonic_halide, Conjugated_double_bond, Halogen_on_hetero O=[SH](=O)F 2 398 410
10 O Sulfonic_halide, Conjugated_double_bond O=[SH](=O)F 2 398 410
11 O Sulfonic_halide, Conjugated_double_bond O=[SH](=O)F 2 398 410
12 F Sulfonic_halide, Halogen_on_hetero O=[SH](=O)F 2 398 410
0 C Alkyne C#C 1 400 842
1 C Alkyne C#C 1 400 842
0 C Aromatic cccc 1 404 929
1 C Aromatic cccc 1 404 929
2 C Aromatic cccc 1 404 929
5 C Aromatic cccc 1 404 929
14 C Bromoalkene, Enolester CBr 2 404 929
15 Br Bromoalkene CBr 2 404 929
18 O Enolester, Lactone O 3 404 929
0 C Alkene C=CC 1 405 516
1 C Secondary_carbon, Alkene C=CC 1 405 516
2 C Secondary_carbon C=CC 1 405 516
10 N Urea, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond [nH]c(=O)[nH]c=O 1 408 512
11 C Urea, Oxoarene, Aromatic, Conjugated_double_bond [nH]c(=O)[nH]c=O 1 408 512
12 O Urea, Oxoarene, Conjugated_double_bond [nH]c(=O)[nH]c=O 1 408 512
13 N Lactam, Urea, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond [nH]c(=O)[nH]c=O 1 408 512
14 C Lactam, Oxoarene, Aromatic, Conjugated_double_bond [nH]c(=O)[nH]c=O 1 408 512
15 O Lactam, Oxoarene, Conjugated_double_bond [nH]c(=O)[nH]c=O 1 408 512
27 Cl Alkylchloride Cl 1 409 435
7 O Primary_amide, Conjugated_double_bond O 1 410 429
0 C Primary_carbon, Secondary_carbon CCCC 1 411 669
1 C Primary_carbon, Secondary_carbon CCCC 1 411 669
2 C Secondary_carbon CCCC 1 411 669
3 C Secondary_carbon CCCC 1 411 669
18 S Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 411 669
19 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 411 669
20 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 411 669
21 N Sulfonamide N[SH](=O)=O 2 411 669
22 C Carboxylic_acid, Conjugated_double_bond O=CO 3 411 669
23 O Carboxylic_acid, Conjugated_double_bond O=CO 3 411 669
24 O Carboxylic_acid O=CO 3 411 669
11 C Tertiary_carbon CN 1 412 472
12 N Primary_aliph_amine CN 1 412 472
3 O Ketone, Conjugated_double_bond O 1 415 546
10 Cl Arylchloride Cl 2 415 546
14 C Primary_carbon C 3 415 546
15 C Primary_carbon C 4 415 546
0 C Primary_carbon, Secondary_carbon CCCC(O)O 1 418 435
1 C Primary_carbon, Secondary_carbon CCCC(O)O 1 418 435
2 C Secondary_carbon CCCC(O)O 1 418 435
3 C Secondary_carbon, Acetal, Acetal_like CCCC(O)O 1 418 435
4 O Acetal, Acetal_like, Heterocyclic CCCC(O)O 1 418 435
29 O Acetal, Acetal_like, Heterocyclic CCCC(O)O 1 418 435
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 420 652
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 420 652
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 420 652
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 420 652
13 C Conjugated_double_bond, Conjugated_tripple_bond C=CC#N 2 420 652
14 C Conjugated_double_bond, Conjugated_tripple_bond C=CC#N 2 420 652
15 C Nitrile, Conjugated_double_bond, Conjugated_tripple_bond C=CC#N 2 420 652
16 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond C=CC#N 2 420 652
10 C Alkylfluoride, Trifluoromethyl FC(F)F 1 421 570
11 F Alkylfluoride, Trifluoromethyl FC(F)F 1 421 570
12 F Alkylfluoride, Trifluoromethyl FC(F)F 1 421 570
13 F Alkylfluoride, Trifluoromethyl FC(F)F 1 421 570
18 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 2 421 570
19 O Anion O=[NH+][O-] 2 421 570
20 O Conjugated_double_bond O=[NH+][O-] 2 421 570
18 C Secondary_carbon, Tertiary_carbon C1CC1 1 423 903
19 C Secondary_carbon, Tertiary_carbon C1CC1 1 423 903
20 C Secondary_carbon, Tertiary_carbon C1CC1 1 423 903
0 C Primary_carbon C 1 425 804
11 C Carboxylic_acid O=CO 2 425 804
12 O Carboxylic_acid O=CO 2 425 804
13 O Carboxylic_acid O=CO 2 425 804
23 Cl Arylchloride Cl 3 425 804
24 O Secondary_alcohol, 1,2-Aminoalcohol O 4 425 804
0 C Primary_carbon, Secondary_carbon CCC(C)NC 1 426 629
1 C Primary_carbon, Secondary_carbon CCC(C)NC 1 426 629
2 C Primary_carbon, Secondary_carbon, Tertiary_amide CCC(C)NC 1 426 629
3 C Primary_carbon CCC(C)NC 1 426 629
4 N Tertiary_amide CCC(C)NC 1 426 629
5 C Tertiary_amide CCC(C)NC 1 426 629
7 O Tertiary_amide, Conjugated_double_bond O 2 426 629
11 C Aromatic cccc 3 426 629
12 C Aromatic cccc 3 426 629
13 C Aromatic cccc 3 426 629
14 C Aromatic cccc 3 426 629
23 Cl Arylchloride Cl 4 426 629
0 C NA C1CN1 1 427 429
1 C NA C1CN1 1 427 429
2 N Tertiary_mixed_amine, Heterocyclic C1CN1 1 427 429
9 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 2 427 429
10 O Anion O=[NH+][O-] 2 427 429
11 O Conjugated_double_bond O=[NH+][O-] 2 427 429
12 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 3 427 429
13 O Anion O=[NH+][O-] 3 427 429
14 O Conjugated_double_bond O=[NH+][O-] 3 427 429
16 O Primary_amide, Conjugated_double_bond O 4 427 429
7 N Amidine, Conjugated_double_bond N 1 429 556
0 C Primary_carbon, Secondary_carbon CCCCO 1 430 857
1 C Primary_carbon, Secondary_carbon CCCCO 1 430 857
2 C Secondary_carbon CCCCO 1 430 857
3 C Secondary_carbon, Alkylarylether CCCCO 1 430 857
4 O Alkylarylether CCCCO 1 430 857
11 O Alkylarylether CO 2 430 857
12 C Alkylarylether CO 2 430 857
0 C Primary_carbon, Tertiary_carbon C 1 435 784
24 O Secondary_alcohol O 1 438 446
16 Cl Arylchloride Cl 1 442 772
12 Br Arylbromide Br 1 443 458
23 O Ketone O 1 446 594
0 C Primary_carbon C 1 447 455
20 Cl Arylchloride Cl 1 449 699
0 C NA CNC 1 450 486
1 N Tertiary_aliph_amine CNC 1 450 486
2 C NA CNC 1 450 486
6 Cl Arylchloride Cl 1 451 464
7 N Urethan, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond [nH]c(=O)o 2 451 464
8 C Urethan, Oxoarene, Aromatic, Conjugated_double_bond [nH]c(=O)o 2 451 464
9 O Urethan, Oxoarene, Conjugated_double_bond [nH]c(=O)o 2 451 464
10 O Urethan, Hetero_O, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond [nH]c(=O)o 2 451 464
6 N Amidine, Heterocyclic NC=N[SH](=O)=O 1 452 460
7 C Amidine, Conjugated_double_bond NC=N[SH](=O)=O 1 452 460
8 N Amidine, Heterocyclic, Conjugated_double_bond NC=N[SH](=O)=O 1 452 460
9 S Heterocyclic, Conjugated_double_bond NC=N[SH](=O)=O 1 452 460
10 O Conjugated_double_bond NC=N[SH](=O)=O 1 452 460
11 O Conjugated_double_bond NC=N[SH](=O)=O 1 452 460
12 S Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 452 460
13 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 452 460
14 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 452 460
15 N Sulfonamide N[SH](=O)=O 2 452 460
0 C Primary_carbon Cc1ccsn1 1 453 510
1 C Primary_carbon, Aromatic Cc1ccsn1 1 453 510
2 C Aromatic Cc1ccsn1 1 453 510
3 C Aromatic Cc1ccsn1 1 453 510
6 O Urea O 2 453 510
13 C Aromatic ccnC 3 453 510
14 C Aromatic ccnC 3 453 510
15 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic ccnC 3 453 510
16 C NA ccnC 3 453 510
18 S Hetero_S, Heteroaromatic, Aromatic, Heterocyclic Cc1ccsn1 1 453 510
19 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cc1ccsn1 1 453 510
0 C Secondary_carbon C1CC1 1 454 550
1 C Secondary_carbon C1CC1 1 454 550
2 C Secondary_carbon, Secondary_amide C1CC1 1 454 550
0 C Aromatic c1ccccc1 1 455 467
1 C Aromatic c1ccccc1 1 455 467
2 C Aromatic c1ccccc1 1 455 467
3 C Aromatic c1ccccc1 1 455 467
4 C Aromatic c1ccccc1 1 455 467
5 C Aromatic c1ccccc1 1 455 467
19 Cl Chloroalkene Cl 2 455 467
23 N Primary_aliph_amine, Peptide_N_term N 3 455 467
0 C Primary_carbon C 1 457 530
14 Cl Arylchloride Cl 2 457 530
18 C Secondary_carbon CN1CCCC1 3 457 530
19 C Secondary_carbon CN1CCCC1 3 457 530
20 C Secondary_carbon CN1CCCC1 3 457 530
21 C Secondary_carbon CN1CCCC1 3 457 530
22 N Tertiary_aliph_amine, Heterocyclic CN1CCCC1 3 457 530
23 C NA CN1CCCC1 3 457 530
12 Cl Arylchloride Cl 1 459 853
0 C Primary_carbon, CH-acidic CC=O 1 462 594
1 C Primary_carbon, Carboxylic_ester CC=O 1 462 594
2 O Carboxylic_ester CC=O 1 462 594
24 O Ketone O 2 462 594
0 C Secondary_carbon C1CCCC1 1 463 532
1 C Secondary_carbon C1CCCC1 1 463 532
2 C Secondary_carbon C1CCCC1 1 463 532
3 C Secondary_carbon C1CCCC1 1 463 532
4 C Secondary_carbon C1CCCC1 1 463 532
10 N Primary_arom_amine N 2 463 532
7 O Carboxylic_acid, Conjugated_double_bond O 1 464 556
8 O Carboxylic_acid O 2 464 556
9 Hg Organometallic_compounds, Halogen_on_hetero Cl[Hg] 3 464 556
10 Cl Halogen_on_hetero Cl[Hg] 3 464 556
0 C Primary_carbon, CH-acidic CC(=O)O 1 467 475
1 C Primary_carbon, Carboxylic_ester CC(=O)O 1 467 475
2 O Carboxylic_ester CC(=O)O 1 467 475
3 O Carboxylic_ester CC(=O)O 1 467 475
21 N Oximether, Conjugated_double_bond CON 2 467 475
22 O Oximether CON 2 467 475
23 C Oximether CON 2 467 475
24 C Aromatic, Conjugated_double_bond Nc1nccs1 3 467 475
25 C Aromatic, Conjugated_double_bond Nc1nccs1 3 467 475
26 S Isothiourea, Hetero_S, Heteroaromatic, Aromatic, Heterocyclic Nc1nccs1 3 467 475
27 C Primary_arom_amine, Isothiourea, Aromatic Nc1nccs1 3 467 475
28 N Primary_arom_amine, Isothiourea Nc1nccs1 3 467 475
29 N Isothiourea, Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond Nc1nccs1 3 467 475
0 C NA C 1 471 583
7 C Aromatic c1ccncc1 2 471 583
8 C Aromatic c1ccncc1 2 471 583
9 C Aromatic c1ccncc1 2 471 583
10 C Aromatic c1ccncc1 2 471 583
11 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 2 471 583
12 C Aromatic c1ccncc1 2 471 583
0 C Alkylarylether CO 1 473 654
1 O Alkylarylether CO 1 473 654
25 Cl Arylchloride Cl 2 473 654
13 Cl Arylchloride Cl 1 479 550
19 O Primary_alcohol O 2 479 550
4 C Carboxylic_acid, Conjugated_double_bond O=CO 1 481 579
5 O Carboxylic_acid, Conjugated_double_bond O=CO 1 481 579
6 O Carboxylic_acid O=CO 1 481 579
12 O Phenol O 2 481 579
5 Cl Alkylchloride Cl 1 482 544
13 Br Arylbromide Br 2 482 544
0 C Aromatic c1ccccc1 1 485 551
1 C Aromatic c1ccccc1 1 485 551
2 C Aromatic c1ccccc1 1 485 551
3 C Aromatic c1ccccc1 1 485 551
4 C Aromatic c1ccccc1 1 485 551
5 C Aromatic c1ccccc1 1 485 551
10 C Aromatic ccc(n)Cl 2 485 551
11 C Imidoylhalide_cyclic, Aromatic ccc(n)Cl 2 485 551
12 C Imidoylhalide_cyclic, Arylchloride, Aromatic ccc(n)Cl 2 485 551
13 Cl Imidoylhalide_cyclic, Arylchloride ccc(n)Cl 2 485 551
14 N Imidoylhalide_cyclic, Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ccc(n)Cl 2 485 551
17 O Phenol O 3 485 551
0 C Primary_carbon CCO 1 486 630
1 C Primary_carbon, Carboxylic_ester CCO 1 486 630
2 O Carboxylic_ester CCO 1 486 630
4 O Carboxylic_ester O 2 486 630
6 C Primary_carbon C 3 486 630
7 C Primary_carbon C 4 486 630
15 Cl Arylchloride Cl 5 486 630
2 C NA C 1 487 521
21 Cl Arylchloride Cl 2 487 521
0 C Primary_carbon CC 1 489 593
1 C Primary_carbon CC 1 489 593
10 O Oxoarene, Conjugated_double_bond O 2 489 593
12 C Carboxylic_acid, Conjugated_double_bond O=CO 3 489 593
13 O Carboxylic_acid, Conjugated_double_bond O=CO 3 489 593
14 O Carboxylic_acid O=CO 3 489 593
16 O Acetal, Acetal_like, Heterocyclic OCO 4 489 593
17 C Acetal, Acetal_like OCO 4 489 593
18 O Acetal, Acetal_like, Heterocyclic OCO 4 489 593
0 C Carboxylic_ester C 1 491 540
12 Cl Arylchloride Cl 2 491 540
7 C Primary_carbon, Quaternary_carbon C 1 496 556
8 C Quaternary_carbon, Carboxylic_acid O=CO 2 496 556
9 O Carboxylic_acid O=CO 2 496 556
10 O Carboxylic_acid O=CO 2 496 556
11 O Dialkylether, Heterocyclic O 3 496 556
12 C Quaternary_carbon, Carboxylic_acid O=CO 4 496 556
13 O Carboxylic_acid O=CO 4 496 556
14 O Carboxylic_acid O=CO 4 496 556
7 C Aromatic c1ccccc1 1 501 879
8 C Aromatic c1ccccc1 1 501 879
9 C Aromatic c1ccccc1 1 501 879
10 C Aromatic c1ccccc1 1 501 879
11 C Aromatic c1ccccc1 1 501 879
12 C Aromatic c1ccccc1 1 501 879
14 O NA O 2 501 879
18 O Isourea O 3 501 879
0 C Secondary_carbon C1CCCCC1 1 502 550
1 C Secondary_carbon C1CCCCC1 1 502 550
2 C Secondary_carbon C1CCCCC1 1 502 550
3 C Secondary_carbon C1CCCCC1 1 502 550
4 C Secondary_carbon C1CCCCC1 1 502 550
5 C Secondary_carbon C1CCCCC1 1 502 550
21 O Primary_alcohol O 2 502 550
0 C Secondary_carbon C1CCCC1 1 504 550
1 C Secondary_carbon C1CCCC1 1 504 550
2 C Secondary_carbon C1CCCC1 1 504 550
3 C Secondary_carbon C1CCCC1 1 504 550
4 C Secondary_carbon C1CCCC1 1 504 550
11 Cl Arylchloride Cl 2 504 550
21 O Primary_alcohol O 3 504 550
19 C Alkylarylether C 1 506 657
0 C NA CCN(C)C 1 507 943
1 N Tertiary_aliph_amine CCN(C)C 1 507 943
2 C NA CCN(C)C 1 507 943
3 C Secondary_carbon CCN(C)C 1 507 943
4 C Secondary_carbon CCN(C)C 1 507 943
16 C Aromatic cccc 2 507 943
17 C Aromatic cccc 2 507 943
18 C Aromatic cccc 2 507 943
19 C Aromatic, Conjugated_double_bond cccc 2 507 943
9 C 1,2-Aminoalcohol CN 1 509 943
10 N Primary_aliph_amine, 1,2-Aminoalcohol CN 1 509 943
11 O Secondary_alcohol, 1,2-Aminoalcohol O 2 509 943
13 Cl Arylchloride Cl 1 510 697
6 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 1 512 861
7 O Anion O=[NH+][O-] 1 512 861
8 O Conjugated_double_bond O=[NH+][O-] 1 512 861
9 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 2 512 861
10 O Anion O=[NH+][O-] 2 512 861
11 O Conjugated_double_bond O=[NH+][O-] 2 512 861
0 C Primary_carbon C 1 515 517
3 C Aromatic ccccc 2 515 517
4 C Aromatic ccccc 2 515 517
5 C Aromatic ccccc 2 515 517
6 C Aromatic ccccc 2 515 517
7 C Aromatic ccccc 2 515 517
8 C Aromatic c1ccncc1 3 515 517
9 C Aromatic c1ccncc1 3 515 517
10 C Aromatic c1ccncc1 3 515 517
11 C Aromatic c1ccncc1 3 515 517
12 C Aromatic c1ccncc1 3 515 517
13 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 3 515 517
14 O Dialkylether CN(C)CCO 4 515 517
15 C Dialkylether CN(C)CCO 4 515 517
16 C NA CN(C)CCO 4 515 517
17 N Tertiary_aliph_amine CN(C)CCO 4 515 517
18 C NA CN(C)CCO 4 515 517
19 C NA CN(C)CCO 4 515 517
2 C Primary_carbon C 1 517 589
3 C Secondary_carbon CCC=[NH+][O-] 2 517 589
4 C Secondary_carbon, CH-acidic CCC=[NH+][O-] 2 517 589
5 C Secondary_carbon CCC=[NH+][O-] 2 517 589
6 N N-Oxide, Heterocyclic, Kation CCC=[NH+][O-] 2 517 589
7 O Anion CCC=[NH+][O-] 2 517 589
0 C Primary_carbon CCNCC 1 518 699
1 C Primary_carbon CCNCC 1 518 699
2 N Tertiary_aliph_amine CCNCC 1 518 699
3 C Primary_carbon CCNCC 1 518 699
4 C Primary_carbon CCNCC 1 518 699
8 O Tertiary_amide O 2 518 699
6 C Primary_amide, Conjugated_double_bond NC=O 1 519 600
7 O Primary_amide, Conjugated_double_bond NC=O 1 519 600
8 N Primary_amide NC=O 1 519 600
6 C Secondary_carbon, Tertiary_carbon C1CC1 1 520 630
7 C Secondary_carbon, Tertiary_carbon C1CC1 1 520 630
8 C Secondary_carbon, Tertiary_carbon C1CC1 1 520 630
11 C Amidine, Imidolactam C1=NCCN1 2 520 630
12 N Amidine, Heterocyclic C1=NCCN1 2 520 630
13 C NA C1=NCCN1 2 520 630
14 C NA C1=NCCN1 2 520 630
15 N Amidine, Heterocyclic C1=NCCN1 2 520 630
7 N Primary_arom_amine N 1 522 586
14 O Primary_alcohol O 2 522 586
0 C Primary_carbon, Tertiary_carbon C 1 523 535
11 C Primary_carbon, Quaternary_carbon C 2 523 535
16 C Secondary_carbon, Tertiary_carbon C1CC1 3 523 535
17 C Secondary_carbon, Tertiary_carbon C1CC1 3 523 535
18 C Secondary_carbon, Tertiary_carbon C1CC1 3 523 535
19 O Phenol O 4 523 535
10 O Phenol O 1 525 876
20 O Phenol, 1,2-Diphenol O 2 525 876
3 C Primary_carbon C 1 528 690
15 N Urea, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond [nH]c([nH])=O 2 528 690
16 C Urea, Oxoarene, Aromatic, Conjugated_double_bond [nH]c([nH])=O 2 528 690
17 O Urea, Oxoarene, Conjugated_double_bond [nH]c([nH])=O 2 528 690
18 N Urea, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond [nH]c([nH])=O 2 528 690
0 C NA CN(C)CCO 1 530 540
1 N Tertiary_aliph_amine CN(C)CCO 1 530 540
2 C NA CN(C)CCO 1 530 540
3 C NA CN(C)CCO 1 530 540
4 C Dialkylether CN(C)CCO 1 530 540
5 O Dialkylether CN(C)CCO 1 530 540
13 C Aromatic c1ccccc1 2 530 540
14 C Aromatic c1ccccc1 2 530 540
15 C Aromatic c1ccccc1 2 530 540
16 C Aromatic c1ccccc1 2 530 540
17 C Aromatic c1ccccc1 2 530 540
18 C Aromatic c1ccccc1 2 530 540
0 C Aromatic c1ccccc1 1 531 868
1 C Aromatic c1ccccc1 1 531 868
2 C Aromatic c1ccccc1 1 531 868
3 C Aromatic c1ccccc1 1 531 868
4 C Aromatic c1ccccc1 1 531 868
5 C Aromatic c1ccccc1 1 531 868
7 C Aromatic c1ccccc1 2 531 868
8 C Aromatic c1ccccc1 2 531 868
9 C Aromatic c1ccccc1 2 531 868
10 C Aromatic c1ccccc1 2 531 868
11 C Aromatic c1ccccc1 2 531 868
12 C Aromatic c1ccccc1 2 531 868
14 O NA O 3 531 868
12 C Secondary_carbon, Tertiary_carbon C1CCCC1 1 533 587
13 C Secondary_carbon, Tertiary_carbon C1CCCC1 1 533 587
14 C Secondary_carbon C1CCCC1 1 533 587
15 C Secondary_carbon C1CCCC1 1 533 587
16 C Secondary_carbon, Tertiary_carbon C1CCCC1 1 533 587
0 C Alkyne C 1 534 594
21 C Aromatic cno 2 534 594
22 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cno 2 534 594
23 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond cno 2 534 594
20 O Phenol O 1 535 862
0 C Aromatic c1ccccc1 1 537 742
1 C Aromatic c1ccccc1 1 537 742
2 C Aromatic c1ccccc1 1 537 742
3 C Diarylether, Aromatic c1ccccc1 1 537 742
4 C Aromatic c1ccccc1 1 537 742
5 C Aromatic c1ccccc1 1 537 742
16 C Secondary_carbon C1CCCC1 2 537 742
17 C Secondary_carbon C1CCCC1 2 537 742
18 C Secondary_carbon C1CCCC1 2 537 742
19 C Secondary_carbon C1CCCC1 2 537 742
20 C Secondary_carbon C1CCCC1 2 537 742
23 C Primary_arom_amine, Imidolactam, Aromatic ncncN 3 537 742
24 N Primary_arom_amine ncncN 3 537 742
25 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ncncN 3 537 742
26 C Aromatic ncncN 3 537 742
27 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ncncN 3 537 742
12 O Phenol, 1,2-Diphenol O 1 540 622
22 O Phenol O 1 541 869
19 Cl Arylchloride Cl 1 542 739
0 C Primary_carbon, Secondary_carbon CCC 1 543 623
1 C Primary_carbon, Secondary_carbon CCC 1 543 623
2 C Secondary_carbon CCC 1 543 623
0 C Primary_carbon CC 1 544 556
1 C Primary_carbon, Tertiary_amide CC 1 544 556
3 C Primary_carbon, Tertiary_amide CC 2 544 556
4 C Primary_carbon CC 2 544 556
6 O Tertiary_amide, Conjugated_double_bond O 3 544 556
13 O Alkylarylether CO 4 544 556
14 C Alkylarylether CO 4 544 556
15 O Phenol O 5 544 556
0 C Alkyne C 1 546 621
0 C Primary_carbon, Secondary_carbon C 1 548 621
4 C Secondary_carbon CCC 2 548 621
5 C Primary_carbon, Secondary_carbon CCC 2 548 621
6 C Primary_carbon, Secondary_carbon CCC 2 548 621
0 C Primary_carbon, Tertiary_carbon CCC 1 549 648
1 C Primary_carbon, Secondary_carbon, Tertiary_carbon CCC 1 549 648
2 C Primary_carbon, Tertiary_carbon CCC 1 549 648
7 O Carboxylic_acid O 2 549 648
14 C Secondary_carbon, Aromatic c1ccccc1 3 549 648
15 C Aromatic c1ccccc1 3 549 648
16 C Aromatic c1ccccc1 3 549 648
17 C Aromatic c1ccccc1 3 549 648
18 C Aromatic c1ccccc1 3 549 648
19 C Aromatic c1ccccc1 3 549 648
20 N Primary_aliph_amine, 1,2-Aminoalcohol N 4 549 648
21 O Secondary_alcohol, 1,2-Aminoalcohol O 5 549 648
6 C Aromatic c1ccncc1 1 551 579
7 C Aromatic c1ccncc1 1 551 579
8 C Aromatic c1ccncc1 1 551 579
9 C Aromatic c1ccncc1 1 551 579
10 C Aromatic c1ccncc1 1 551 579
11 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 1 551 579
12 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic [nH]n 1 553 961
13 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic [nH]n 1 553 961
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 555 887
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 555 887
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 555 887
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 555 887
11 C Aromatic cccc 2 555 887
12 C Aromatic cccc 2 555 887
13 C Aromatic cccc 2 555 887
14 C Aromatic cccc 2 555 887
19 C Aromatic ccc 3 555 887
20 C Aromatic ccc 3 555 887
21 C Aromatic ccc 3 555 887
26 O Tertiary_alcohol O 4 555 887
0 C Primary_carbon C 1 556 1008
8 Cl Arylchloride Cl 2 556 1008
9 Cl Arylchloride Cl 3 556 1008
0 C Primary_carbon, Tertiary_carbon CC(C)C 1 558 648
1 C Primary_carbon, Secondary_carbon, Tertiary_carbon CC(C)C 1 558 648
2 C Primary_carbon, Tertiary_carbon CC(C)C 1 558 648
3 C Secondary_carbon, Tertiary_carbon CC(C)C 1 558 648
6 O Secondary_amide O 2 558 648
13 C Guanidine N=CN 3 558 648
14 N Guanidine N=CN 3 558 648
15 N Guanidine N=CN 3 558 648
18 O Secondary_amide O 4 558 648
19 C Dialkylether, Epoxide O=C(O)C1CO1 5 558 648
20 C Dialkylether, Epoxide O=C(O)C1CO1 5 558 648
21 C Carboxylic_acid O=C(O)C1CO1 5 558 648
22 O Carboxylic_acid O=C(O)C1CO1 5 558 648
23 O Carboxylic_acid O=C(O)C1CO1 5 558 648
24 O Dialkylether, Heterocyclic, Epoxide O=C(O)C1CO1 5 558 648
2 C Secondary_carbon, Quaternary_carbon CCNC 1 559 635
3 C Secondary_carbon, Aminal CCNC 1 559 635
4 N Aminal, Acetal_like, Heterocyclic CCNC 1 559 635
5 C Aminal CCNC 1 559 635
8 C Aminal C 2 559 635
17 O Urethan O 3 559 635
18 N Urethan CN 4 559 635
19 C NA CN 4 559 635
35 O Carboxylic_acid O 1 562 801
36 O Carboxylic_acid O 2 562 801
0 C Dialkylether CCCOC 1 564 589
1 O Dialkylether CCCOC 1 564 589
2 C Secondary_carbon, Dialkylether CCCOC 1 564 589
3 C Secondary_carbon CCCOC 1 564 589
4 C Secondary_carbon CCCOC 1 564 589
7 N Oximether, Conjugated_double_bond NCCON 2 564 589
8 O Oximether NCCON 2 564 589
9 C Oximether NCCON 2 564 589
10 C NA NCCON 2 564 589
11 N Primary_aliph_amine NCCON 2 564 589
18 C Alkylfluoride, Trifluoromethyl FC(F)F 3 564 589
19 F Alkylfluoride, Trifluoromethyl FC(F)F 3 564 589
20 F Alkylfluoride, Trifluoromethyl FC(F)F 3 564 589
21 F Alkylfluoride, Trifluoromethyl FC(F)F 3 564 589
0 C Primary_carbon, Secondary_carbon CCCC 1 568 605
1 C Primary_carbon, Secondary_carbon CCCC 1 568 605
2 C Secondary_carbon CCCC 1 568 605
3 C Secondary_carbon CCCC 1 568 605
7 C Primary_carbon, Secondary_alcohol CCO 2 568 605
8 C Primary_carbon CCO 2 568 605
9 O Secondary_alcohol CCO 2 568 605
15 N Primary_arom_amine N 3 568 605
9 C NA C 1 569 886
21 F Arylfluoride F 2 569 886
0 C Primary_carbon C 1 570 650
18 Cl Arylchloride Cl 2 570 650
19 Cl Arylchloride Cl 3 570 650
6 I Aryliodide I 1 572 714
15 Br Arylbromide Br 2 572 714
17 Br Arylbromide Br 3 572 714
0 C Primary_carbon CC 1 573 661
1 C Primary_carbon CC 1 573 661
3 C NA C 2 573 661
4 C NA C 3 573 661
11 O Phenol O 4 573 661
17 O Phenol O 1 577 858
0 C Carboxylic_ester CO 1 578 584
1 O Carboxylic_ester CO 1 578 584
0 C Primary_carbon, Secondary_carbon CCCC 1 579 701
1 C Primary_carbon, Secondary_carbon CCCC 1 579 701
2 C Secondary_carbon CCCC 1 579 701
3 C Secondary_carbon CCCC 1 579 701
8 C Carboxylic_acid, Conjugated_double_bond O=CO 2 579 701
9 O Carboxylic_acid, Conjugated_double_bond O=CO 2 579 701
10 O Carboxylic_acid O=CO 2 579 701
0 C Primary_carbon C 1 582 635
3 C Aromatic ccnc 2 582 635
4 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ccnc 2 582 635
5 C Aromatic ccnc 2 582 635
6 C Aromatic ccnc 2 582 635
13 C Aromatic cccc 3 582 635
14 C Aromatic cccc 3 582 635
15 C Aromatic cccc 3 582 635
16 C Aromatic cccc 3 582 635
3 C Primary_carbon, Quaternary_carbon C 1 583 614
6 O Imide_acidic O 2 583 614
9 O Imide_acidic O 3 583 614
0 C Secondary_amide CNC=O 1 584 597
1 N Secondary_amide CNC=O 1 584 597
2 C Secondary_amide, Conjugated_double_bond CNC=O 1 584 597
3 O Secondary_amide, Conjugated_double_bond CNC=O 1 584 597
0 C Aromatic c1ccoc1 1 585 603
1 C Aromatic c1ccoc1 1 585 603
2 C Aromatic c1ccoc1 1 585 603
11 C Carboxylic_acid, Conjugated_double_bond O=CO 2 585 603
12 O Carboxylic_acid, Conjugated_double_bond O=CO 2 585 603
13 O Carboxylic_acid O=CO 2 585 603
14 O NA NS(=O)O 3 585 603
15 S NA NS(=O)O 3 585 603
16 O NA NS(=O)O 3 585 603
17 N NA NS(=O)O 3 585 603
18 Cl Arylchloride Cl 4 585 603
19 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic c1ccoc1 1 585 603
20 C Aromatic c1ccoc1 1 585 603
0 C Primary_carbon C 1 587 605
8 C Aromatic c1ccoc1 2 587 605
9 C Aromatic c1ccoc1 2 587 605
10 C Aromatic c1ccoc1 2 587 605
11 C Aromatic c1ccoc1 2 587 605
12 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic c1ccoc1 2 587 605
0 C Primary_alcohol OCC(O)CO 1 588 868
1 C NA OCC(O)CO 1 588 868
2 C Primary_alcohol OCC(O)CO 1 588 868
3 O Primary_alcohol OCC(O)CO 1 588 868
4 O NA OCC(O)CO 1 588 868
11 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nc(N)[nH]c=O 2 588 868
12 C Primary_arom_amine, Aromatic, Conjugated_double_bond nc(N)[nH]c=O 2 588 868
13 N Primary_arom_amine nc(N)[nH]c=O 2 588 868
14 N Lactam, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond nc(N)[nH]c=O 2 588 868
15 C Lactam, Oxoarene, Aromatic, Conjugated_double_bond nc(N)[nH]c=O 2 588 868
16 O Lactam, Oxoarene, Conjugated_double_bond nc(N)[nH]c=O 2 588 868
17 O Primary_alcohol OCC(O)CO 1 588 868
8 O Carboxylic_acid O 1 589 969
9 O Carboxylic_acid O 2 589 969
10 C Quaternary_carbon CN 3 589 969
11 N Primary_aliph_amine CN 3 589 969
24 Cl Arylchloride Cl 1 590 816
19 O Secondary_alcohol O 1 592 744
6 C Aromatic cnncNN 1 593 602
7 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cnncNN 1 593 602
8 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cnncNN 1 593 602
9 C Imidolactam, Aromatic cnncNN 1 593 602
10 N Hydrazine cnncNN 1 593 602
11 N Hydrazine cnncNN 1 593 602
24 O Secondary_alcohol O 1 594 723
0 C Primary_carbon, Tertiary_carbon CCC 1 595 661
1 C Primary_carbon, Tertiary_carbon CCC 1 595 661
2 C Primary_carbon, Tertiary_carbon CCC 1 595 661
12 C Tertiary_carbon, Ketone, Conjugated_double_bond CC(C)C=O 2 595 661
13 O Ketone, Conjugated_double_bond CC(C)C=O 2 595 661
14 C Primary_carbon, Tertiary_carbon, Ketone, CH-acidic CC(C)C=O 2 595 661
15 C Primary_carbon, Tertiary_carbon CC(C)C=O 2 595 661
16 C Primary_carbon, Tertiary_carbon CC(C)C=O 2 595 661
0 C Primary_carbon ccncC 1 597 614
1 C Primary_carbon, Aromatic ccncC 1 597 614
4 C Aromatic ccncC 1 597 614
5 C Aromatic ccncC 1 597 614
6 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ccncC 1 597 614
8 C Aromatic cccc 2 597 614
9 C Aromatic cccc 2 597 614
10 C Aromatic cccc 2 597 614
11 C Aromatic cccc 2 597 614
15 I Aryliodide I 1 600 601
17 O Phenol O 1 601 633
6 N Acetal_like, NOS_methylen_ester_and_similar, Hetero_methylen_ester_and_similar, Heterocyclic NCN[SH](=O)=O 1 602 607
7 C Acetal_like, NOS_methylen_ester_and_similar, Hetero_methylen_ester_and_similar NCN[SH](=O)=O 1 602 607
8 N Acetal_like, NOS_methylen_ester_and_similar, Hetero_methylen_ester_and_similar, Sulfonamide, Heterocyclic NCN[SH](=O)=O 1 602 607
9 S Sulfonamide, Heterocyclic, Conjugated_double_bond NCN[SH](=O)=O 1 602 607
10 O Sulfonamide, Conjugated_double_bond NCN[SH](=O)=O 1 602 607
11 O Sulfonamide, Conjugated_double_bond NCN[SH](=O)=O 1 602 607
12 S Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 602 607
13 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 602 607
14 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 602 607
15 N Sulfonamide N[SH](=O)=O 2 602 607
16 Cl Arylchloride Cl 3 602 607
17 O Phenol O 1 603 818
2 C Primary_carbon, Tertiary_carbon C 1 605 860
0 C Primary_carbon CC(C)NN 1 606 629
1 C Primary_carbon CC(C)NN 1 606 629
2 C Primary_carbon CC(C)NN 1 606 629
3 N NA CC(C)NN 1 606 629
4 N NA CC(C)NN 1 606 629
6 O Conjugated_double_bond O 2 606 629
6 I Aryliodide I 1 607 716
9 C Guanidine NCN 2 607 716
10 N Guanidine NCN 2 607 716
11 N Guanidine NCN 2 607 716
0 C Primary_carbon Cc1ccno1 1 610 620
1 C Primary_carbon, Aromatic, Conjugated_double_bond Cc1ccno1 1 610 620
2 C Aromatic, Conjugated_double_bond Cc1ccno1 1 610 620
3 C Aromatic, Conjugated_double_bond Cc1ccno1 1 610 620
4 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic Cc1ccno1 1 610 620
5 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic Cc1ccno1 1 610 620
15 C Alkylfluoride, Trifluoromethyl FC(F)F 2 610 620
16 F Alkylfluoride, Trifluoromethyl FC(F)F 2 610 620
17 F Alkylfluoride, Trifluoromethyl FC(F)F 2 610 620
18 F Alkylfluoride, Trifluoromethyl FC(F)F 2 610 620
0 C Primary_carbon, Tertiary_carbon CC(C)C 1 612 1014
1 C Primary_carbon, Secondary_carbon, Tertiary_carbon CC(C)C 1 612 1014
2 C Primary_carbon, Tertiary_carbon CC(C)C 1 612 1014
3 C Secondary_carbon, Tertiary_carbon CC(C)C 1 612 1014
11 C Primary_carbon, Tertiary_carbon C 2 612 1014
12 C Tertiary_carbon, Carboxylic_acid O=CO 3 612 1014
13 O Carboxylic_acid O=CO 3 612 1014
14 O Carboxylic_acid O=CO 3 612 1014
8 O Imidoacid_cyclic, Phenol O 1 613 937
0 C Alkene C 1 614 786
8 C Secondary_carbon, Tertiary_carbon CC(=O)O 2 614 786
9 C Secondary_carbon, Carboxylic_acid CC(=O)O 2 614 786
10 O Carboxylic_acid CC(=O)O 2 614 786
11 O Carboxylic_acid CC(=O)O 2 614 786
12 C Carboxylic_acid, Alpha_aminoacid O=CO 3 614 786
13 O Carboxylic_acid, Alpha_aminoacid O=CO 3 614 786
14 O Carboxylic_acid, Alpha_aminoacid O=CO 3 614 786
0 C NA C1=NCCN1 1 617 980
1 C NA C1=NCCN1 1 617 980
2 N Guanidine, Heterocyclic C1=NCCN1 1 617 980
3 C Guanidine C1=NCCN1 1 617 980
4 N Guanidine, Heterocyclic C1=NCCN1 1 617 980
12 Cl Arylchloride Cl 2 617 980
13 I Aryliodide I 3 617 980
14 Cl Arylchloride Cl 4 617 980
18 I Aryliodide I 1 618 749
3 C Primary_carbon CC 1 620 707
4 C Primary_carbon CC 1 620 707
11 C Primary_carbon C 2 620 707
0 C Primary_carbon, Secondary_carbon C 1 621 881
10 O Phenol, 1,2-Diphenol O 2 621 881
11 O Phenol, 1,2-Diphenol O 3 621 881
12 O Secondary_alcohol, 1,2-Aminoalcohol O 4 621 881
12 I Aryliodide I 1 622 631
0 C Primary_carbon, Quaternary_carbon C 1 623 815
10 O Ketone, Conjugated_double_bond O 2 623 815
11 Cl Arylchloride Cl 3 623 815
12 Cl Arylchloride Cl 4 623 815
15 C Carboxylic_acid O=CO 5 623 815
16 O Carboxylic_acid O=CO 5 623 815
17 O Carboxylic_acid O=CO 5 623 815
18 C Secondary_carbon, Tertiary_carbon, Quaternary_carbon C1CCCC1 6 623 815
19 C Secondary_carbon, Tertiary_carbon C1CCCC1 6 623 815
20 C Secondary_carbon C1CCCC1 6 623 815
21 C Secondary_carbon C1CCCC1 6 623 815
22 C Secondary_carbon, Tertiary_carbon C1CCCC1 6 623 815
0 C Primary_carbon CCO 1 627 890
1 C Primary_carbon, Urethan CCO 1 627 890
2 O Urethan CCO 1 627 890
4 O Urethan O 2 627 890
19 C Aromatic cccn 3 627 890
20 C Aromatic cccn 3 627 890
21 C Aromatic cccn 3 627 890
22 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond cccn 3 627 890
24 Cl Arylchloride Cl 4 627 890
0 C Primary_carbon, Secondary_carbon CCC 1 629 642
1 C Primary_carbon, Secondary_carbon CCC 1 629 642
2 C Secondary_carbon CCC 1 629 642
7 C Primary_carbon, Secondary_carbon C 2 629 642
10 C Aromatic c1ccccc1 3 629 642
11 C Aromatic c1ccccc1 3 629 642
12 C Aromatic c1ccccc1 3 629 642
13 C Aromatic c1ccccc1 3 629 642
14 C Aromatic c1ccccc1 3 629 642
15 C Aromatic c1ccccc1 3 629 642
17 C Carboxylic_ester, Conjugated_double_bond CCCOC=O 4 629 642
18 O Carboxylic_ester, Conjugated_double_bond CCCOC=O 4 629 642
19 O Carboxylic_ester CCCOC=O 4 629 642
20 C Secondary_carbon, Carboxylic_ester CCCOC=O 4 629 642
21 C Primary_carbon, Secondary_carbon CCCOC=O 4 629 642
22 C Primary_carbon, Secondary_carbon CCCOC=O 4 629 642
23 C Carbothioic_S_ester, Conjugated_double_bond CCSC=O 5 629 642
24 O Carbothioic_S_ester, Conjugated_double_bond CCSC=O 5 629 642
25 S Carbothioic_S_ester CCSC=O 5 629 642
26 C Primary_carbon, Carbothioic_S_ester CCSC=O 5 629 642
27 C Primary_carbon CCSC=O 5 629 642
0 C Primary_carbon C 1 630 815
6 C Primary_carbon C 2 630 815
10 C Primary_carbon CCN 3 630 815
11 C Primary_carbon CCN 3 630 815
12 N Primary_aliph_amine CCN 3 630 815
13 C Carboxylic_ester C 1 631 645
16 C Alkylarylether C 1 633 839
0 C Primary_carbon C 1 634 782
9 C Amidine, Imidolactam, Conjugated_double_bond C1=NCCN1 2 634 782
10 N Amidine, Heterocyclic, Conjugated_double_bond C1=NCCN1 2 634 782
11 C NA C1=NCCN1 2 634 782
12 C NA C1=NCCN1 2 634 782
13 N Amidine, Heterocyclic C1=NCCN1 2 634 782
0 C Alkylarylether C 1 635 653
0 C Aromatic c1ccccc1 1 639 716
1 C Aromatic c1ccccc1 1 639 716
2 C Aromatic c1ccccc1 1 639 716
3 C Secondary_amide, Aromatic c1ccccc1 1 639 716
4 C Aromatic c1ccccc1 1 639 716
5 C Aromatic c1ccccc1 1 639 716
8 O Secondary_amide, Conjugated_double_bond O 2 639 716
15 Cl Arylchloride Cl 3 639 716
16 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 4 639 716
17 O Anion O=[NH+][O-] 4 639 716
18 O Conjugated_double_bond O=[NH+][O-] 4 639 716
0 C Primary_carbon, Tertiary_carbon CCC 1 641 855
1 C Primary_carbon, Tertiary_carbon CCC 1 641 855
2 C Primary_carbon, Tertiary_carbon CCC 1 641 855
30 N Tertiary_mixed_amine CNC 2 641 855
31 C NA CNC 2 641 855
32 C NA CNC 2 641 855
16 N Secondary_aliph_amine, Heterocyclic N 1 642 957
0 C NA CCNC 1 646 952
1 N Secondary_aliph_amine CCNC 1 646 952
2 C Secondary_carbon CCNC 1 646 952
3 C Secondary_carbon CCNC 1 646 952
6 C Secondary_carbon, Quaternary_carbon CC 2 646 952
7 C Secondary_carbon, Tertiary_carbon CC 2 646 952
0 C NA CNC 1 647 737
1 N Urethan CNC 1 647 737
2 C NA CNC 1 647 737
4 O Urethan O 2 647 737
12 N Ammonium, Kation C[N+](C)C 3 647 737
13 C NA C[N+](C)C 3 647 737
14 C NA C[N+](C)C 3 647 737
15 C NA C[N+](C)C 3 647 737
7 S Thionitrite, Nitroso O=NS 1 648 720
8 N Thionitrite, Nitroso O=NS 1 648 720
9 O Thionitrite, Nitroso O=NS 1 648 720
11 O Secondary_amide O 2 648 720
12 N Secondary_amide, Peptide_C_term NCC(=O)O 3 648 720
13 C Secondary_amide, Peptide_C_term NCC(=O)O 3 648 720
14 C Carboxylic_acid, Peptide_C_term NCC(=O)O 3 648 720
15 O Carboxylic_acid, Peptide_C_term NCC(=O)O 3 648 720
16 O Carboxylic_acid, Peptide_C_term NCC(=O)O 3 648 720
19 O Carboxylic_acid, Alpha_aminoacid O 4 648 720
20 O Carboxylic_acid, Alpha_aminoacid O 5 648 720
21 N Primary_aliph_amine, Alpha_aminoacid N 6 648 720
1 C Secondary_carbon CC(N)C(=O)O 1 649 667
2 C Secondary_carbon, Alpha_aminoacid CC(N)C(=O)O 1 649 667
3 C Carboxylic_acid, Alpha_aminoacid CC(N)C(=O)O 1 649 667
4 O Carboxylic_acid, Alpha_aminoacid CC(N)C(=O)O 1 649 667
5 O Carboxylic_acid, Alpha_aminoacid CC(N)C(=O)O 1 649 667
6 N Primary_aliph_amine, Alpha_aminoacid CC(N)C(=O)O 1 649 667
9 C Guanidine NCN[N+](=O)[O-] 2 649 667
10 N Guanidine NCN[N+](=O)[O-] 2 649 667
11 N Guanidine, Nitro NCN[N+](=O)[O-] 2 649 667
12 N Nitro, Kation NCN[N+](=O)[O-] 2 649 667
13 O Anion NCN[N+](=O)[O-] 2 649 667
14 O NA NCN[N+](=O)[O-] 2 649 667
0 C NA CN 1 652 785
1 N Secondary_aliph_amine CN 1 652 785
13 C Aromatic ccnc 2 652 785
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ccnc 2 652 785
15 C Aromatic ccnc 2 652 785
16 C Aromatic ccnc 2 652 785
12 O Phenol O 1 653 786
31 F Arylfluoride F 1 654 811
0 C Primary_carbon, Quaternary_carbon C 1 655 707
2 C Primary_carbon, Quaternary_carbon C 2 655 707
13 C Secondary_carbon CC(=O)O 3 655 707
14 C Secondary_carbon, Carboxylic_acid CC(=O)O 3 655 707
15 O Carboxylic_acid CC(=O)O 3 655 707
16 O Carboxylic_acid CC(=O)O 3 655 707
0 C Aromatic cccc 1 656 827
1 C Aromatic cccc 1 656 827
2 C Aromatic cccc 1 656 827
9 C Aromatic cccc 1 656 827
0 C Alkene C=C 1 657 666
1 C Alkene C=C 1 657 666
0 C Primary_carbon, Secondary_carbon C 1 658 702
6 C Primary_carbon, Secondary_carbon C 2 658 702
8 O Tertiary_amide O 3 658 702
10 C Secondary_carbon CCC(=O)O 4 658 702
11 C Secondary_carbon CCC(=O)O 4 658 702
12 C Secondary_carbon, Carboxylic_acid CCC(=O)O 4 658 702
13 O Carboxylic_acid CCC(=O)O 4 658 702
14 O Carboxylic_acid CCC(=O)O 4 658 702
3 C Aromatic c[nH]n 1 661 950
4 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic c[nH]n 1 661 950
5 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c[nH]n 1 661 950
9 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 2 661 950
10 O Anion O=[NH+][O-] 2 661 950
11 O Conjugated_double_bond O=[NH+][O-] 2 661 950
21 O Alkylarylether CO 1 662 936
22 C Alkylarylether CO 1 662 936
23 O Alkylarylether CO 2 662 936
24 C Alkylarylether CO 2 662 936
25 O Alkylarylether CO 3 662 936
26 C Alkylarylether CO 3 662 936
7 O Ketone, Conjugated_double_bond O 1 664 853
12 C Aromatic cccc 2 664 853
13 C Aromatic cccc 2 664 853
14 C Aromatic cccc 2 664 853
15 C Aromatic cccc 2 664 853
19 C Aromatic c1ccccc1 3 664 853
20 C Aromatic c1ccccc1 3 664 853
21 C Aromatic c1ccccc1 3 664 853
22 C Aromatic c1ccccc1 3 664 853
23 C Aromatic c1ccccc1 3 664 853
24 C Aromatic c1ccccc1 3 664 853
9 O Phenol, 1,2-Diphenol O 1 668 881
10 O Phenol, 1,2-Diphenol O 2 668 881
11 C Carboxylic_acid, Alpha_aminoacid O=CO 3 668 881
12 O Carboxylic_acid, Alpha_aminoacid O=CO 3 668 881
13 O Carboxylic_acid, Alpha_aminoacid O=CO 3 668 881
0 C NA CS(N)(=O)=O 1 669 737
1 S Sulfonamide CS(N)(=O)=O 1 669 737
2 O Sulfonamide CS(N)(=O)=O 1 669 737
3 O Sulfonamide CS(N)(=O)=O 1 669 737
4 N Sulfonamide CS(N)(=O)=O 1 669 737
12 C Diarylether, Aromatic c1ccccc1 2 669 737
13 C Aromatic c1ccccc1 2 669 737
14 C Aromatic c1ccccc1 2 669 737
15 C Aromatic c1ccccc1 2 669 737
16 C Aromatic c1ccccc1 2 669 737
17 C Aromatic c1ccccc1 2 669 737
18 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 3 669 737
19 O Anion O=[NH+][O-] 3 669 737
20 O Conjugated_double_bond O=[NH+][O-] 3 669 737
0 C Aromatic c1ccccc1 1 670 707
1 C Aromatic c1ccccc1 1 670 707
2 C Aromatic c1ccccc1 1 670 707
3 C Secondary_carbon, Aromatic c1ccccc1 1 670 707
4 C Aromatic c1ccccc1 1 670 707
5 C Aromatic c1ccccc1 1 670 707
17 O Carboxylic_acid, Conjugated_double_bond O 2 670 707
18 O Carboxylic_acid O 3 670 707
19 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 4 670 707
20 O Anion O=[NH+][O-] 4 670 707
21 O Conjugated_double_bond O=[NH+][O-] 4 670 707
0 C Aromatic c1ccccc1 1 674 771
1 C Aromatic c1ccccc1 1 674 771
2 C Aromatic c1ccccc1 1 674 771
3 C Quaternary_carbon, Aromatic c1ccccc1 1 674 771
4 C Aromatic c1ccccc1 1 674 771
5 C Aromatic c1ccccc1 1 674 771
17 N Tertiary_aliph_amine, Heterocyclic C1COCCN1 2 674 771
18 C NA C1COCCN1 2 674 771
19 C Dialkylether C1COCCN1 2 674 771
20 O Dialkylether, Heterocyclic C1COCCN1 2 674 771
21 C Dialkylether C1COCCN1 2 674 771
22 C NA C1COCCN1 2 674 771
0 C Primary_carbon, Ketone, CH-acidic CC=O 1 676 952
1 C Primary_carbon, Tertiary_carbon, Ketone CC=O 1 676 952
2 O Ketone CC=O 1 676 952
19 O Ketone O 2 676 952
17 C Primary_alcohol, 1,2-Aminoalcohol CO 1 677 721
18 O Primary_alcohol, 1,2-Aminoalcohol CO 1 677 721
0 C Primary_carbon, Ketone, CH-acidic CC(C)=O 1 680 860
1 C Primary_carbon, Secondary_carbon, Ketone CC(C)=O 1 680 860
2 O Ketone CC(C)=O 1 680 860
3 C Secondary_carbon, Ketone, CH-acidic CC(C)=O 1 680 860
4 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nnn 1 681 767
5 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nnn 1 681 767
6 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nnn 1 681 767
0 C Primary_carbon C 1 684 851
6 C Primary_carbon C 2 684 851
12 C Tertiary_carbon, Alkene, Lactone, Conjugated_double_bond C=CC(=O)O 3 684 851
13 C Alkene, Conjugated_double_bond C=CC(=O)O 3 684 851
14 C Lactone, Conjugated_double_bond C=CC(=O)O 3 684 851
15 O Lactone, Conjugated_double_bond C=CC(=O)O 3 684 851
16 O Lactone, Heterocyclic C=CC(=O)O 3 684 851
17 O Dialkylether, Heterocyclic, Epoxide O 4 684 851
21 O Carboxylic_acid O 1 686 959
23 C NA C[N+](C)(C)C 2 686 959
24 N Quaternary_aliph_ammonium, Ammonium, Kation C[N+](C)(C)C 2 686 959
25 C NA C[N+](C)(C)C 2 686 959
26 C NA C[N+](C)(C)C 2 686 959
27 C NA C[N+](C)(C)C 2 686 959
6 O Oxoarene, Conjugated_double_bond O 1 688 698
13 O Acetal, Acetal_like, Heterocyclic OCO 2 688 698
14 C Acetal, Acetal_like OCO 2 688 698
15 O Acetal, Acetal_like, Heterocyclic OCO 2 688 698
16 C Carboxylic_acid, Conjugated_double_bond O=CO 3 688 698
17 O Carboxylic_acid, Conjugated_double_bond O=CO 3 688 698
18 O Carboxylic_acid O=CO 3 688 698
0 C NA CC[N+](C)(C)C 1 689 691
1 N Quaternary_aliph_ammonium, Ammonium, Kation CC[N+](C)(C)C 1 689 691
2 C NA CC[N+](C)(C)C 1 689 691
3 C NA CC[N+](C)(C)C 1 689 691
4 C NA CC[N+](C)(C)C 1 689 691
5 C Alkyne CC[N+](C)(C)C 1 689 691
14 C Aromatic cc[nH] 1 690 717
15 C Aromatic cc[nH] 1 690 717
16 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic cc[nH] 1 690 717
0 C Primary_carbon C 1 693 837
0 C Primary_carbon, Secondary_carbon CCC 1 695 701
1 C Primary_carbon, Secondary_carbon CCC 1 695 701
2 C Secondary_carbon CCC 1 695 701
17 C Aromatic c[nH] 2 695 701
18 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic c[nH] 2 695 701
19 C Tertiary_carbon, Dialkylthioether CSC 3 695 701
20 S Dialkylthioether CSC 3 695 701
21 C Dialkylthioether CSC 3 695 701
6 C Aromatic cccn 1 696 698
7 C Aromatic cccn 1 696 698
8 C Aromatic cccn 1 696 698
9 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cccn 1 696 698
8 N Guanidine N 1 697 707
9 N Guanidine N=C(N)N 2 697 707
10 C Guanidine N=C(N)N 2 697 707
11 N Guanidine N=C(N)N 2 697 707
12 N Guanidine N=C(N)N 2 697 707
0 C Primary_carbon, Secondary_carbon CCC 1 698 896
1 C Primary_carbon, Secondary_carbon CCC 1 698 896
2 C Secondary_carbon CCC 1 698 896
13 C Aromatic cn[nH] 2 698 896
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cn[nH] 2 698 896
15 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic cn[nH] 2 698 896
0 C Primary_carbon, Secondary_carbon CC 1 699 768
1 C Primary_carbon, Secondary_carbon, Ketone, CH-acidic CC 1 699 768
3 O Ketone, Conjugated_double_bond O 2 699 768
14 O Lactam, Oxoarene, Conjugated_double_bond O 1 701 862
16 N Primary_arom_amine N 1 702 758
17 O Phenol O 1 705 718
18 O Phenol O 2 705 718
19 O Phenol O 3 705 718
21 O Phenol, 1,2-Diphenol O 4 705 718
0 C Primary_carbon, Secondary_carbon CCCN 1 707 796
1 C Primary_carbon, Secondary_carbon CCCN 1 707 796
2 C Secondary_carbon CCCN 1 707 796
3 N Secondary_aliph_amine CCCN 1 707 796
5 C Primary_carbon C 2 707 796
15 C Primary_carbon C 3 707 796
0 C Primary_carbon, Secondary_carbon CC 1 708 796
1 C Primary_carbon, Secondary_carbon CC 1 708 796
17 C Aromatic ccccO 2 708 796
18 C Aromatic ccccO 2 708 796
19 C Aromatic ccccO 2 708 796
20 C Phenol, Aromatic ccccO 2 708 796
21 O Phenol ccccO 2 708 796
10 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 1 711 715
11 O Anion O=[NH+][O-] 1 711 715
12 O Conjugated_double_bond O=[NH+][O-] 1 711 715
13 N Heterocyclic C1CNCCN1 2 711 715
14 C NA C1CNCCN1 2 711 715
15 C NA C1CNCCN1 2 711 715
16 N Secondary_aliph_amine, Heterocyclic C1CNCCN1 2 711 715
17 C NA C1CNCCN1 2 711 715
18 C NA C1CNCCN1 2 711 715
0 C Primary_carbon, Secondary_carbon CCC 1 715 896
1 C Primary_carbon, Secondary_carbon CCC 1 715 896
2 C Secondary_carbon CCC 1 715 896
13 C Aromatic cnc(n)N 2 715 896
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cnc(n)N 2 715 896
15 C Primary_arom_amine, Aromatic cnc(n)N 2 715 896
16 N Primary_arom_amine cnc(n)N 2 715 896
17 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cnc(n)N 2 715 896
0 C Alkyne C#C 1 716 1008
1 C Alkyne C#C 1 716 1008
4 C NA C 2 716 1008
13 C Aromatic cccc 1 717 903
14 C Aromatic cccc 1 717 903
15 C Aromatic cccc 1 717 903
16 C Aromatic cccc 1 717 903
0 C Alkylarylether C 1 718 933
19 N Primary_arom_amine N 2 718 933
22 Cl Arylchloride Cl 1 721 813
20 C Ketone O=CCO 1 723 867
21 O Ketone O=CCO 1 723 867
22 C Primary_alcohol, Ketone O=CCO 1 723 867
23 O Primary_alcohol O=CCO 1 723 867
24 O Tertiary_alcohol O 2 723 867
14 O Phenol, 1,2-Diphenol O 1 725 935
16 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 2 725 935
17 O Anion O=[NH+][O-] 2 725 935
18 O Conjugated_double_bond O=[NH+][O-] 2 725 935
19 F Arylfluoride F 3 725 935
0 C Acetal CO 1 730 992
1 O Acetal, Acetal_like CO 1 730 992
12 C Amidine, Imidolactam C1=NCCN1 2 730 992
13 N Amidine, Heterocyclic C1=NCCN1 2 730 992
14 C NA C1=NCCN1 2 730 992
15 C NA C1=NCCN1 2 730 992
16 N Amidine, Heterocyclic C1=NCCN1 2 730 992
12 N Sulfonamide CS(N)(=O)=O 1 731 751
13 S Sulfonamide CS(N)(=O)=O 1 731 751
14 O Sulfonamide CS(N)(=O)=O 1 731 751
15 O Sulfonamide CS(N)(=O)=O 1 731 751
16 C NA CS(N)(=O)=O 1 731 751
8 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl F 1 737 815
9 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl F 2 737 815
10 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl F 3 737 815
11 S Isothiourea, Hetero_S, Heteroaromatic, Aromatic, Heterocyclic nc(N)s 4 737 815
12 C Primary_arom_amine, Isothiourea, Aromatic nc(N)s 4 737 815
13 N Primary_arom_amine, Isothiourea nc(N)s 4 737 815
14 N Isothiourea, Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nc(N)s 4 737 815
0 C Primary_carbon C 1 739 765
19 Cl Arylchloride Cl 2 739 765
8 O Alkylarylether OC1CCCC1 1 742 756
9 C Secondary_carbon, Alkylarylether OC1CCCC1 1 742 756
10 C Secondary_carbon OC1CCCC1 1 742 756
11 C Secondary_carbon OC1CCCC1 1 742 756
12 C Secondary_carbon OC1CCCC1 1 742 756
13 C Secondary_carbon OC1CCCC1 1 742 756
14 C Secondary_carbon, Tertiary_carbon O=C1CCCN1 2 742 756
15 C Secondary_carbon, Tertiary_carbon, Lactam O=C1CCCN1 2 742 756
16 C Secondary_carbon, Lactam O=C1CCCN1 2 742 756
17 O Lactam O=C1CCCN1 2 742 756
18 N Lactam, Heterocyclic O=C1CCCN1 2 742 756
19 C Tertiary_carbon O=C1CCCN1 2 742 756
9 O Dialkylether, Heterocyclic, Epoxide O 1 744 838
19 Cl Arylchloride Cl 1 749 750
20 Cl Arylchloride Cl 2 749 750
21 O Phenol O 3 749 750
13 C Primary_alcohol CO 1 751 760
14 O Primary_alcohol CO 1 751 760
15 O Phenol O 2 751 760
0 C Alkylarylether CO 1 756 792
1 O Alkylarylether CO 1 756 792
8 N Tertiary_mixed_amine, Heterocyclic C1CNCCN1 2 756 792
9 C NA C1CNCCN1 2 756 792
10 C NA C1CNCCN1 2 756 792
11 N Secondary_aliph_amine, Heterocyclic C1CNCCN1 2 756 792
12 C NA C1CNCCN1 2 756 792
13 C NA C1CNCCN1 2 756 792
0 C Primary_carbon CCN(C)CC 1 758 1008
1 C Primary_carbon CCN(C)CC 1 758 1008
2 N Tertiary_aliph_amine CCN(C)CC 1 758 1008
3 C Primary_carbon CCN(C)CC 1 758 1008
4 C Primary_carbon CCN(C)CC 1 758 1008
5 C NA CCN(C)CC 1 758 1008
9 O Secondary_amide, Conjugated_double_bond O 2 758 1008
16 O Alkylarylether CO 3 758 1008
17 C Alkylarylether CO 3 758 1008
18 S Sulfon, Conjugated_double_bond C[SH](=O)=O 4 758 1008
19 O Conjugated_double_bond C[SH](=O)=O 4 758 1008
20 O Conjugated_double_bond C[SH](=O)=O 4 758 1008
21 C CH-acidic C[SH](=O)=O 4 758 1008
9 N Tertiary_aliph_amine, Heterocyclic C1CCNCC1 1 759 881
10 C Secondary_carbon C1CCNCC1 1 759 881
11 C Secondary_carbon C1CCNCC1 1 759 881
12 C Secondary_carbon C1CCNCC1 1 759 881
13 C Secondary_carbon C1CCNCC1 1 759 881
14 C Secondary_carbon C1CCNCC1 1 759 881
15 C Secondary_carbon, Tertiary_carbon C1CCCCC1 2 759 881
16 C Secondary_carbon, Tertiary_carbon C1CCCCC1 2 759 881
17 C Secondary_carbon C1CCCCC1 2 759 881
18 C Secondary_carbon C1CCCCC1 2 759 881
19 C Secondary_carbon C1CCCCC1 2 759 881
20 C Secondary_carbon, Tertiary_carbon C1CCCCC1 2 759 881
21 O Tertiary_alcohol O 3 759 881
13 O Phenol O 1 760 769
14 O Phenol O 2 760 769
0 C Primary_carbon C 1 762 782
10 N Tertiary_aliph_amine, Heterocyclic C1CCNC1 2 762 782
11 C Secondary_carbon C1CCNC1 2 762 782
12 C Secondary_carbon C1CCNC1 2 762 782
13 C Secondary_carbon C1CCNC1 2 762 782
14 C Secondary_carbon C1CCNC1 2 762 782
15 C Aromatic, Conjugated_double_bond c1ccncc1 3 762 782
16 C Aromatic, Conjugated_double_bond c1ccncc1 3 762 782
17 C Aromatic c1ccncc1 3 762 782
18 C Aromatic c1ccncc1 3 762 782
19 C Aromatic c1ccncc1 3 762 782
20 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond c1ccncc1 3 762 782
0 C NA C 1 765 776
19 C Alkylarylether C 2 765 776
21 C Alkylarylether C 3 765 776
10 C Tertiary_carbon, Amidine, Imidolactam C1=NCCN1 1 766 909
11 N Amidine, Heterocyclic C1=NCCN1 1 766 909
12 C NA C1=NCCN1 1 766 909
13 C NA C1=NCCN1 1 766 909
14 N Amidine, Heterocyclic C1=NCCN1 1 766 909
3 C Primary_carbon C 1 769 881
13 Cl Arylchloride Cl 2 769 881
14 O Secondary_alcohol, 1,2-Aminoalcohol O 3 769 881
0 C Primary_carbon C 1 771 800
4 C Primary_carbon C 2 771 800
16 O Alkylarylether CO 3 771 800
17 C Alkylarylether CO 3 771 800
19 Cl Arylchloride Cl 4 771 800
0 C Primary_carbon, Secondary_carbon CCCCN 1 772 785
1 C Primary_carbon, Secondary_carbon CCCCN 1 772 785
2 C Secondary_carbon CCCCN 1 772 785
3 C Secondary_carbon CCCCN 1 772 785
4 N NA CCCCN 1 772 785
6 O NA O 2 772 785
0 C Primary_carbon, Tertiary_carbon C 1 773 887
13 C Secondary_carbon, Aromatic c1ccccc1 1 774 785
14 C Aromatic c1ccccc1 1 774 785
15 C Aromatic c1ccccc1 1 774 785
16 C Aromatic c1ccccc1 1 774 785
17 C Aromatic c1ccccc1 1 774 785
18 C Aromatic c1ccccc1 1 774 785
17 Cl Arylchloride Cl 1 776 870
0 C Primary_carbon CCNCC 1 778 878
1 C Primary_carbon CCNCC 1 778 878
2 N NA CCNCC 1 778 878
3 C Primary_carbon CCNCC 1 778 878
4 C Primary_carbon CCNCC 1 778 878
6 S NA S 2 778 878
10 S NA S 3 778 878
11 N NA CCNCC 4 778 878
12 C Primary_carbon CCNCC 4 778 878
13 C Primary_carbon CCNCC 4 778 878
14 C Primary_carbon CCNCC 4 778 878
15 C Primary_carbon CCNCC 4 778 878
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 805
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 805
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 805
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 805
18 C Primary_carbon, Quaternary_carbon CC(C)C 2 782 805
19 C Primary_carbon, Quaternary_carbon CC(C)C 2 782 805
20 C Primary_carbon, Quaternary_carbon CC(C)C 2 782 805
21 C Primary_carbon, Quaternary_carbon CC(C)C 2 782 805
15 C Ketone O=CCO 1 784 975
16 O Ketone O=CCO 1 784 975
17 C Primary_alcohol, Ketone O=CCO 1 784 975
18 O Primary_alcohol O=CCO 1 784 975
24 F Alkylfluoride F 2 784 975
25 O Secondary_alcohol O 3 784 975
26 O Tertiary_alcohol, 1,2-Diol O 4 784 975
27 O Secondary_alcohol, 1,2-Diol O 5 784 975
9 C Carboxylic_acid, Alpha_aminoacid O=CO 1 786 832
10 O Carboxylic_acid, Alpha_aminoacid O=CO 1 786 832
11 O Carboxylic_acid, Alpha_aminoacid O=CO 1 786 832
0 C Aromatic c1ccccc1 1 791 840
1 C Aromatic c1ccccc1 1 791 840
2 C Aromatic c1ccccc1 1 791 840
3 C Aromatic c1ccccc1 1 791 840
4 C Aromatic c1ccccc1 1 791 840
5 C Aromatic c1ccccc1 1 791 840
12 C Primary_arom_amine, Imidolactam, Aromatic nc(N)ncN 2 791 840
13 N Primary_arom_amine nc(N)ncN 2 791 840
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nc(N)ncN 2 791 840
15 C Primary_arom_amine, Aromatic nc(N)ncN 2 791 840
16 N Primary_arom_amine nc(N)ncN 2 791 840
17 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nc(N)ncN 2 791 840
6 C Alkylfluoride, Trifluoromethyl FC(F)F 1 792 815
7 F Alkylfluoride, Trifluoromethyl FC(F)F 1 792 815
8 F Alkylfluoride, Trifluoromethyl FC(F)F 1 792 815
9 F Alkylfluoride, Trifluoromethyl FC(F)F 1 792 815
10 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1cncn1 2 792 815
11 C Aromatic c1cncn1 2 792 815
12 C Aromatic c1cncn1 2 792 815
13 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1cncn1 2 792 815
14 C Aromatic c1cncn1 2 792 815
0 C Primary_carbon C 1 793 911
9 C Secondary_carbon CCNC 2 793 911
10 C Secondary_carbon CCNC 2 793 911
11 N Secondary_aliph_amine CCNC 2 793 911
12 C NA CCNC 2 793 911
0 C Primary_carbon, Secondary_carbon C 1 794 805
4 C Aromatic, Conjugated_double_bond c1ccccc1 2 794 805
5 C Aromatic, Conjugated_double_bond c1ccccc1 2 794 805
6 C Aromatic c1ccccc1 2 794 805
7 C Aromatic c1ccccc1 2 794 805
8 C Aromatic c1ccccc1 2 794 805
9 C Aromatic, Conjugated_double_bond c1ccccc1 2 794 805
17 C Alkylarylether CCN(C)C 3 794 805
18 C NA CCN(C)C 3 794 805
19 N Tertiary_aliph_amine CCN(C)C 3 794 805
20 C NA CCN(C)C 3 794 805
21 C NA CCN(C)C 3 794 805
22 C Aromatic, Conjugated_double_bond c1ccccc1 4 794 805
23 C Aromatic, Conjugated_double_bond c1ccccc1 4 794 805
24 C Aromatic c1ccccc1 4 794 805
25 C Aromatic c1ccccc1 4 794 805
26 C Aromatic c1ccccc1 4 794 805
27 C Aromatic, Conjugated_double_bond c1ccccc1 4 794 805
0 C Carboxylic_ester COC=O 1 799 885
1 O Carboxylic_ester COC=O 1 799 885
2 C Tertiary_carbon, Carboxylic_ester COC=O 1 799 885
3 O Carboxylic_ester COC=O 1 799 885
18 O Secondary_alcohol O 2 799 885
0 C Primary_carbon, Secondary_carbon CCCCN 1 800 894
1 C Primary_carbon, Secondary_carbon CCCCN 1 800 894
2 C Secondary_carbon CCCCN 1 800 894
3 C Secondary_carbon CCCCN 1 800 894
4 N Secondary_mixed_amine CCCCN 1 800 894
12 O Carboxylic_ester, Conjugated_double_bond O 2 800 894
14 C Carboxylic_ester CCN(C)C 3 800 894
15 C NA CCN(C)C 3 800 894
16 N Tertiary_aliph_amine CCN(C)C 3 800 894
17 C NA CCN(C)C 3 800 894
18 C NA CCN(C)C 3 800 894
9 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N 1 805 1014
10 C Thioamide, Conjugated_double_bond NC=S 2 805 1014
11 S Thioamide, Conjugated_double_bond NC=S 2 805 1014
12 N Thioamide NC=S 2 805 1014
6 C Secondary_carbon CCCO 1 809 826
7 C Secondary_carbon CCCO 1 809 826
8 C Secondary_carbon, Dialkylether CCCO 1 809 826
9 O Dialkylether, Heterocyclic CCCO 1 809 826
0 C Secondary_carbon CCC 1 815 950
1 C Secondary_carbon, Tertiary_carbon CCC 1 815 950
4 C Secondary_carbon, Tertiary_carbon C 2 815 950
7 C Secondary_carbon, Tertiary_carbon CCC 1 815 950
11 C NA S=CS 3 815 950
12 S NA S=CS 3 815 950
13 S NA S=CS 3 815 950
0 C Primary_carbon, Secondary_carbon CCC 1 818 820
1 C Primary_carbon, Secondary_carbon CCC 1 818 820
2 C Secondary_carbon CCC 1 818 820
4 C Secondary_carbon CCC 2 818 820
5 C Primary_carbon, Secondary_carbon CCC 2 818 820
6 C Primary_carbon, Secondary_carbon CCC 2 818 820
13 C Phenol, Aromatic OccccF 3 818 820
14 C Aromatic OccccF 3 818 820
15 C Aromatic OccccF 3 818 820
16 C Arylfluoride, Aromatic OccccF 3 818 820
17 F Arylfluoride OccccF 3 818 820
18 O Phenol OccccF 3 818 820
0 C Primary_carbon C 1 820 980
6 C Primary_carbon C 2 820 980
9 C Isothiourea C1=NCCCS1 3 820 980
10 N Isothiourea, Heterocyclic C1=NCCCS1 3 820 980
11 C Secondary_carbon C1=NCCCS1 3 820 980
12 C Secondary_carbon C1=NCCCS1 3 820 980
13 C Secondary_carbon C1=NCCCS1 3 820 980
14 S Isothiourea, Heterocyclic C1=NCCCS1 3 820 980
6 C Primary_carbon C 1 827 950
9 C Secondary_carbon, Amidine, Imidolactam C1=NCCN1 2 827 950
10 N Amidine, Heterocyclic C1=NCCN1 2 827 950
11 C NA C1=NCCN1 2 827 950
12 C NA C1=NCCN1 2 827 950
13 N Amidine, Heterocyclic C1=NCCN1 2 827 950
14 C Primary_carbon, Quaternary_carbon CC(C)C 3 827 950
15 C Primary_carbon, Quaternary_carbon CC(C)C 3 827 950
16 C Primary_carbon, Quaternary_carbon CC(C)C 3 827 950
17 C Primary_carbon, Quaternary_carbon CC(C)C 3 827 950
0 C NA CCN(C)C 1 831 835
1 N Tertiary_aliph_amine CCN(C)C 1 831 835
2 C NA CCN(C)C 1 831 835
3 C NA CCN(C)C 1 831 835
4 C Alkene, Conjugated_double_bond CCN(C)C 1 831 835
12 Br Arylbromide Br 2 831 835
13 C Aromatic, Conjugated_double_bond c1ccncc1 3 831 835
14 C Aromatic, Conjugated_double_bond c1ccncc1 3 831 835
15 C Aromatic c1ccncc1 3 831 835
16 C Aromatic c1ccncc1 3 831 835
17 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 3 831 835
18 C Aromatic, Conjugated_double_bond c1ccncc1 3 831 835
0 C NA CCN(C)C 1 834 957
1 N Tertiary_aliph_amine CCN(C)C 1 834 957
2 C NA CCN(C)C 1 834 957
3 C Secondary_carbon CCN(C)C 1 834 957
4 C Secondary_carbon CCN(C)C 1 834 957
0 C Alkylarylether CO 1 835 845
1 O Alkylarylether CO 1 835 845
9 O Alkyl_imide, Conjugated_double_bond O 2 835 845
10 N Alkyl_imide, Heterocyclic O=C1CCCN1 3 835 845
11 C Secondary_carbon, Alkyl_imide O=C1CCCN1 3 835 845
12 C Secondary_carbon O=C1CCCN1 3 835 845
13 C Secondary_carbon, CH-acidic O=C1CCCN1 3 835 845
14 C Secondary_carbon, Alkyl_imide O=C1CCCN1 3 835 845
15 O Alkyl_imide O=C1CCCN1 3 835 845
0 C NA CN 1 838 843
1 N Tertiary_aliph_amine, Heterocyclic CN 1 838 843
0 C Primary_carbon CC=O 1 839 953
1 C Primary_carbon, Secondary_amide CC=O 1 839 953
2 O Secondary_amide CC=O 1 839 953
4 C Primary_carbon C 1 840 841
5 C Primary_carbon C 2 840 841
0 C Primary_carbon, Tertiary_carbon CNCC(C)C 1 841 861
1 C Primary_carbon, Tertiary_carbon CNCC(C)C 1 841 861
2 C Primary_carbon, Tertiary_carbon CNCC(C)C 1 841 861
3 C Tertiary_carbon CNCC(C)C 1 841 861
4 N NA CNCC(C)C 1 841 861
5 C NA CNCC(C)C 1 841 861
8 Cl Imidoylhalide_cyclic, Arylchloride Cl 2 841 861
12 N Primary_arom_amine N 3 841 861
14 C Conjugated_double_bond NC(N)=NC=O 4 841 861
15 O Conjugated_double_bond NC(N)=NC=O 4 841 861
16 N Guanidine, Conjugated_double_bond NC(N)=NC=O 4 841 861
17 C Guanidine, Conjugated_double_bond NC(N)=NC=O 4 841 861
18 N Guanidine NC(N)=NC=O 4 841 861
19 N Guanidine NC(N)=NC=O 4 841 861
0 C NA CCCN(C)C 1 842 1008
1 N Tertiary_aliph_amine, Heterocyclic CCCN(C)C 1 842 1008
2 C Secondary_carbon CCCN(C)C 1 842 1008
3 C Secondary_carbon CCCN(C)C 1 842 1008
4 C Secondary_carbon, Alkene, Conjugated_double_bond CCCN(C)C 1 842 1008
6 C NA CCCN(C)C 1 842 1008
8 O Carboxylic_ester, Conjugated_double_bond O 2 842 1008
9 O Carboxylic_ester CO 3 842 1008
10 C Carboxylic_ester CO 3 842 1008
4 C Secondary_carbon CC 1 843 856
5 C Secondary_carbon CC 1 843 856
14 C Tertiary_carbon, Primary_alcohol CO 2 843 856
15 O Primary_alcohol CO 2 843 856
6 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nnnN 1 844 950
7 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nnnN 1 844 950
8 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic nnnN 1 844 950
9 N NA nnnN 1 844 950
0 C Primary_carbon CCS(N)(=O)=O 1 845 850
1 C Primary_carbon CCS(N)(=O)=O 1 845 850
2 S Sulfonamide CCS(N)(=O)=O 1 845 850
3 O Sulfonamide CCS(N)(=O)=O 1 845 850
4 O Sulfonamide CCS(N)(=O)=O 1 845 850
5 N Sulfonamide CCS(N)(=O)=O 1 845 850
13 C Secondary_carbon, Alkene, Conjugated_double_bond C1CCCCC1 2 845 850
14 C Secondary_carbon C1CCCCC1 2 845 850
15 C Secondary_carbon C1CCCCC1 2 845 850
16 C Secondary_carbon C1CCCCC1 2 845 850
17 C Secondary_carbon C1CCCCC1 2 845 850
18 C Secondary_carbon C1CCCCC1 2 845 850
19 C Aromatic, Conjugated_double_bond c1c[nH]cn1 3 845 850
20 C Aromatic, Conjugated_double_bond c1c[nH]cn1 3 845 850
21 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1c[nH]cn1 3 845 850
22 C Aromatic c1c[nH]cn1 3 845 850
23 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond c1c[nH]cn1 3 845 850
0 C Alkene C=CC 1 848 870
1 C Alkene C=CC 1 848 870
2 C NA C=CC 1 848 870
12 Cl Arylchloride Cl 2 848 870
0 C Secondary_carbon C1CCNCC1 1 850 875
1 C Secondary_carbon C1CCNCC1 1 850 875
2 C Secondary_carbon, Tertiary_amide C1CCNCC1 1 850 875
3 N Tertiary_amide, Heterocyclic C1CCNCC1 1 850 875
4 C Secondary_carbon, Tertiary_amide C1CCNCC1 1 850 875
5 C Secondary_carbon C1CCNCC1 1 850 875
14 O Alkylarylether, Heterocyclic OCCO 2 850 875
15 C Alkylarylether OCCO 2 850 875
16 C Alkylarylether OCCO 2 850 875
17 O Alkylarylether, Heterocyclic OCCO 2 850 875
0 C Enolether CO 1 851 897
1 O Enolether CO 1 851 897
13 O Ketone, Conjugated_double_bond O 2 851 897
14 O Enolether CO 3 851 897
15 C Enolether CO 3 851 897
17 O Phenol O 1 858 929
18 O Phenol O 2 858 929
0 C Primary_carbon, Secondary_carbon CC 1 860 865
1 C Primary_carbon, Secondary_carbon CC 1 860 865
11 C Primary_carbon, Secondary_carbon C 2 860 865
6 N Lactam, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond [nH]c(=O)c([nH])=O 1 861 868
7 C Lactam, Oxoarene, Aromatic, Conjugated_double_bond [nH]c(=O)c([nH])=O 1 861 868
8 O Lactam, Oxoarene, Conjugated_double_bond [nH]c(=O)c([nH])=O 1 861 868
9 C Lactam, Oxoarene, Aromatic, Conjugated_double_bond [nH]c(=O)c([nH])=O 1 861 868
10 O Lactam, Oxoarene, Conjugated_double_bond [nH]c(=O)c([nH])=O 1 861 868
11 N Lactam, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond [nH]c(=O)c([nH])=O 1 861 868
17 C Alkylarylether C 1 862 869
0 C Primary_carbon CC 1 867 971
1 C Primary_carbon, Alkene, Conjugated_double_bond CC 1 867 971
4 O Ketone, Conjugated_double_bond O 2 867 971
13 O Ketone, Conjugated_double_bond O 3 867 971
17 C Primary_carbon, Quaternary_carbon C 4 867 971
22 C Primary_carbon, Quaternary_carbon C 5 867 971
0 C Primary_carbon CCnc([nH])=O 1 868 937
1 C Primary_carbon CCnc([nH])=O 1 868 937
2 N Urea, Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond CCnc([nH])=O 1 868 937
9 N Urea, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond CCnc([nH])=O 1 868 937
10 C Urea, Oxoarene, Aromatic, Conjugated_double_bond CCnc([nH])=O 1 868 937
11 O Urea, Oxoarene, Conjugated_double_bond CCnc([nH])=O 1 868 937
12 Cl Arylchloride Cl 2 868 937
13 Cl Arylchloride Cl 3 868 937
0 C Primary_carbon, Secondary_carbon CC 1 869 927
1 C Primary_carbon, Secondary_carbon CC 1 869 927
0 C Aromatic c1ccccc1 1 870 887
1 C Aromatic c1ccccc1 1 870 887
2 C Aromatic c1ccccc1 1 870 887
3 C Tertiary_carbon, Aromatic c1ccccc1 1 870 887
4 C Aromatic c1ccccc1 1 870 887
5 C Aromatic c1ccccc1 1 870 887
17 O Phenol, 1,2-Diphenol O 2 870 887
18 O Phenol, 1,2-Diphenol O 3 870 887
0 C Primary_carbon cnnCC 1 871 896
1 C Primary_carbon cnnCC 1 871 896
2 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic cnnCC 1 871 896
5 C Aromatic cnnCC 1 871 896
6 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cnnCC 1 871 896
11 C Carboxylic_ester, Conjugated_double_bond CCOC=O 2 871 896
12 O Carboxylic_ester, Conjugated_double_bond CCOC=O 2 871 896
13 O Carboxylic_ester CCOC=O 2 871 896
14 C Primary_carbon, Carboxylic_ester CCOC=O 2 871 896
15 C Primary_carbon CCOC=O 2 871 896
16 N Hydrazone CC(C)=NN 3 871 896
17 N Hydrazone CC(C)=NN 3 871 896
18 C Primary_carbon, Hydrazone CC(C)=NN 3 871 896
19 C Primary_carbon, CH-acidic CC(C)=NN 3 871 896
20 C Primary_carbon, CH-acidic CC(C)=NN 3 871 896
0 C Primary_carbon, Tertiary_carbon CCC(=O)O 1 875 935
1 C Primary_carbon, Tertiary_carbon CCC(=O)O 1 875 935
16 C Tertiary_carbon, Carboxylic_acid CCC(=O)O 1 875 935
17 O Carboxylic_acid CCC(=O)O 1 875 935
18 O Carboxylic_acid CCC(=O)O 1 875 935
5 C Primary_carbon C 1 881 894
13 I Aryliodide I 2 881 894
0 C Aromatic c1ccccc1 1 893 897
1 C Aromatic c1ccccc1 1 893 897
2 C Aromatic c1ccccc1 1 893 897
3 C Aromatic c1ccccc1 1 893 897
4 C Aromatic c1ccccc1 1 893 897
5 C Aromatic c1ccccc1 1 893 897
12 O Oxoarene, Conjugated_double_bond O 2 893 897
15 N Heterocyclic C1COCCN1 3 893 897
16 C NA C1COCCN1 3 893 897
17 C Dialkylether C1COCCN1 3 893 897
18 O Dialkylether, Heterocyclic C1COCCN1 3 893 897
19 C Dialkylether C1COCCN1 3 893 897
20 C NA C1COCCN1 3 893 897
0 C Primary_carbon CC(C)N 1 894 969
1 C Primary_carbon CC(C)N 1 894 969
2 C Primary_carbon CC(C)N 1 894 969
3 N Secondary_aliph_amine, 1,2-Aminoalcohol CC(C)N 1 894 969
12 O Phenol, 1,2-Diphenol O 2 894 969
14 O Secondary_alcohol, 1,2-Aminoalcohol O 3 894 969
7 O Oxoarene, Conjugated_double_bond O 1 896 1013
0 C Primary_carbon C 1 897 1009
2 C Primary_carbon C 2 897 1009
14 O Ketone, Conjugated_double_bond O 3 897 1009
16 O Ketone, Conjugated_double_bond O 4 897 1009
0 C Primary_carbon CNC(C)C 1 903 984
1 C Primary_carbon CNC(C)C 1 903 984
2 C Primary_carbon CNC(C)C 1 903 984
3 N Secondary_aliph_amine, 1,2-Aminoalcohol CNC(C)C 1 903 984
4 C 1,2-Aminoalcohol CNC(C)C 1 903 984
14 C Secondary_carbon CCOC 2 903 984
15 C Secondary_carbon, Dialkylether CCOC 2 903 984
16 O Dialkylether CCOC 2 903 984
17 C Dialkylether CCOC 2 903 984
18 O Secondary_alcohol, 1,2-Aminoalcohol O 3 903 984
0 C Primary_carbon C 1 906 963
5 C Nitrile, Conjugated_tripple_bond C#N 2 906 963
6 N Nitrile, Conjugated_tripple_bond C#N 2 906 963
8 O Lactam, Oxoarene, Conjugated_double_bond O 3 906 963
10 C Aromatic c1ccncc1 4 906 963
11 C Aromatic c1ccncc1 4 906 963
12 C Aromatic c1ccncc1 4 906 963
13 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 4 906 963
14 C Aromatic c1ccncc1 4 906 963
15 C Aromatic c1ccncc1 4 906 963
0 C Primary_carbon, Quaternary_carbon C 1 909 954
2 C Primary_carbon, Quaternary_carbon C 2 909 954
7 C Primary_carbon, Quaternary_carbon C 3 909 954
12 C Primary_carbon C 4 909 954
0 C Alkylarylether C 1 910 1025
7 O Ketone, Conjugated_double_bond O 2 910 1025
16 O Phenol O 3 910 1025
17 O Alkylarylether CO 4 910 1025
18 C Alkylarylether CO 4 910 1025
23 O Phenol O 5 910 1025
6 C Primary_carbon, Quaternary_carbon C 1 911 934
7 C Primary_carbon, Quaternary_carbon C 2 911 934
15 C Secondary_carbon, Tertiary_carbon C1=CCCC1 1 913 959
16 C Tertiary_carbon, Alkene C1=CCCC1 1 913 959
17 C Secondary_carbon, Alkene C1=CCCC1 1 913 959
18 C Secondary_carbon C1=CCCC1 1 913 959
19 C Secondary_carbon, Tertiary_carbon C1=CCCC1 1 913 959
0 C Alkylarylether C 1 919 933
20 C Alkylarylether C 2 919 933
32 O Secondary_alcohol O 1 920 1010
0 C Alkylarylether CO 1 921 929
1 O Alkylarylether CO 1 921 929
17 O Phenol, 1,2-Diphenol O 2 921 929
18 O Phenol, 1,2-Diphenol O 3 921 929
19 O Alkylarylether CO 4 921 929
20 C Alkylarylether CO 4 921 929
0 C Primary_carbon C=CC(C)(C)O 1 922 929
1 C Primary_carbon, Alkylarylether C=CC(C)(C)O 1 922 929
2 C Primary_carbon C=CC(C)(C)O 1 922 929
3 C Alkene, Conjugated_double_bond C=CC(C)(C)O 1 922 929
4 C Alkene, Conjugated_double_bond C=CC(C)(C)O 1 922 929
8 C Secondary_carbon CCC(C)(C)O 2 922 929
9 C Secondary_carbon CCC(C)(C)O 2 922 929
10 C Primary_carbon, Secondary_carbon, Alkylarylether CCC(C)(C)O 2 922 929
11 C Primary_carbon CCC(C)(C)O 2 922 929
12 C Primary_carbon CCC(C)(C)O 2 922 929
13 O Alkylarylether, Heterocyclic CCC(C)(C)O 2 922 929
28 O Phenol, 1,2-Diphenol O 3 922 929
29 O Phenol, 1,2-Diphenol O 4 922 929
30 O Alkylarylether, Heterocyclic C=CC(C)(C)O 1 922 929
0 C Alkylarylether CO 1 924 1009
1 O Alkylarylether CO 1 924 1009
17 O Alkylarylether CO 2 924 1009
18 C Alkylarylether CO 2 924 1009
19 O Alkylarylether CO 3 924 1009
20 C Alkylarylether CO 3 924 1009
21 O Phenol O 4 924 1009
0 C NA CCNC 1 927 952
1 N Tertiary_aliph_amine, Heterocyclic CCNC 1 927 952
2 C Secondary_carbon CCNC 1 927 952
3 C Secondary_carbon CCNC 1 927 952
15 O Phenol O 2 927 952
17 C Alkylarylether C 3 927 952
21 O Alkylarylether CO 4 927 952
22 C Alkylarylether CO 4 927 952
23 O Alkylarylether CO 5 927 952
24 C Alkylarylether CO 5 927 952
2 C Secondary_carbon, Tertiary_carbon CCC(=O)OC 1 928 1017
3 C Secondary_carbon, CH-acidic CCC(=O)OC 1 928 1017
4 C Secondary_carbon, Carboxylic_ester CCC(=O)OC 1 928 1017
5 O Carboxylic_ester CCC(=O)OC 1 928 1017
6 O Carboxylic_ester CCC(=O)OC 1 928 1017
7 C Carboxylic_ester CCC(=O)OC 1 928 1017
18 O Secondary_alcohol O 2 928 1017
21 C Secondary_carbon, Quaternary_carbon CCC(C)O 3 928 1017
22 C Secondary_carbon CCC(C)O 3 928 1017
23 C Secondary_carbon, Secondary_alcohol CCC(C)O 3 928 1017
24 C Secondary_carbon, Tertiary_carbon CCC(C)O 3 928 1017
28 O Secondary_alcohol O 4 928 1017
29 O Secondary_alcohol CCC(C)O 3 928 1017
33 O Secondary_alcohol O 1 930 983
24 O Ketone O 1 931 945
28 C Primary_carbon, Carboxylic_ester CC=O 2 931 945
29 O Carboxylic_ester CC=O 2 931 945
30 C Primary_carbon, CH-acidic CC=O 2 931 945
0 C Primary_carbon CC=C(C)C 1 932 1009
1 C Primary_carbon, Alkene CC=C(C)C 1 932 1009
2 C Secondary_carbon, Alkene CC=C(C)C 1 932 1009
3 C Secondary_carbon CC=C(C)C 1 932 1009
10 O Phenol O 2 932 1009
15 C Secondary_carbon CC=C(C)C 3 932 1009
16 C Secondary_carbon, Alkene CC=C(C)C 3 932 1009
17 C Primary_carbon, Alkene CC=C(C)C 3 932 1009
18 C Primary_carbon CC=C(C)C 3 932 1009
19 C Primary_carbon CC=C(C)C 3 932 1009
25 O Phenol O 4 932 1009
26 O Alkylarylether CO 5 932 1009
27 C Alkylarylether CO 5 932 1009
28 O Phenol O 6 932 1009
29 C Primary_carbon CC=C(C)C 1 932 1009
6 O Phenol, 1,2-Diphenol O 1 933 989
7 O Phenol, 1,2-Diphenol O 2 933 989
8 O Phenol, 1,2-Diphenol O 3 933 989
20 O Phenol O 4 933 989
24 C Alkylarylether C 1 934 939
26 C Alkylarylether C 2 934 939
0 C Alkylarylether CO 1 935 949
1 O Alkylarylether CO 1 935 949
9 O Ketone, Conjugated_double_bond O 2 935 949
10 C Ketone, Aromatic, Conjugated_double_bond c1ccccc1 3 935 949
11 C Aromatic, Conjugated_double_bond c1ccccc1 3 935 949
12 C Aromatic c1ccccc1 3 935 949
13 C Aromatic c1ccccc1 3 935 949
14 C Aromatic c1ccccc1 3 935 949
15 C Aromatic, Conjugated_double_bond c1ccccc1 3 935 949
16 O Phenol O 4 935 949
11 O Alkylarylether CO 1 937 1013
12 C Alkylarylether CO 1 937 1013
13 O Alkylarylether CO 2 937 1013
14 C Alkylarylether CO 2 937 1013
0 C Primary_carbon, CH-acidic CC=O 1 940 965
1 C Primary_carbon, Carboxylic_ester CC=O 1 940 965
2 O Carboxylic_ester CC=O 1 940 965
33 O Carboxylic_ester CC(=O)O 2 940 965
34 C Primary_carbon, Carboxylic_ester CC(=O)O 2 940 965
35 O Carboxylic_ester CC(=O)O 2 940 965
36 C Primary_carbon, CH-acidic CC(=O)O 2 940 965
33 O Tertiary_alcohol O 1 941 985
0 C Alkene C 1 943 952
13 C Primary_carbon, Quaternary_carbon C 2 943 952
14 O Dialkylether, Heterocyclic, Epoxide O 3 943 952
0 C NA CCNC 1 948 1012
1 N Tertiary_aliph_amine, Heterocyclic CCNC 1 948 1012
2 C Secondary_carbon CCNC 1 948 1012
3 C Secondary_carbon, Quaternary_carbon CCNC 1 948 1012
19 O Phenol O 2 948 1012
20 O Alkylarylether CO 3 948 1012
21 C Alkylarylether CO 3 948 1012
22 O Enolether CO 4 948 1012
23 C Enolether CO 4 948 1012
0 C Alkene C=CC(C)(C)O 1 949 950
1 C Alkene C=CC(C)(C)O 1 949 950
2 C Primary_carbon, Secondary_carbon, Tertiary_alcohol C=CC(C)(C)O 1 949 950
3 C Primary_carbon C=CC(C)(C)O 1 949 950
4 C Secondary_carbon C=CC(C)(C)O 1 949 950
8 C Alkene C 2 949 950
12 C Primary_carbon, Secondary_carbon, Tertiary_carbon, Quaternary_carbon CCCC(C)C 3 949 950
13 C Primary_carbon, Quaternary_carbon CCCC(C)C 3 949 950
14 C Primary_carbon, Quaternary_carbon CCCC(C)C 3 949 950
15 C Secondary_carbon, Quaternary_carbon CCCC(C)C 3 949 950
16 C Secondary_carbon CCCC(C)C 3 949 950
17 C Secondary_carbon, Quaternary_carbon CCCC(C)C 3 949 950
21 O Tertiary_alcohol C=CC(C)(C)O 1 949 950
0 C Primary_carbon C 1 950 969
9 O Carboxylic_acid O 2 950 969
0 C Alkylarylether CO 1 951 987
1 O Alkylarylether CO 1 951 987
13 C Aromatic cco 2 951 987
14 C Aromatic cco 2 951 987
15 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic cco 2 951 987
21 O Lactone, Oxoarene, Conjugated_double_bond O 3 951 987
22 O Acetal, Acetal_like, Heterocyclic OCO 4 951 987
23 C Acetal, Acetal_like OCO 4 951 987
24 O Acetal, Acetal_like, Heterocyclic OCO 4 951 987
11 C Secondary_carbon, Tertiary_carbon CCC=O 1 952 957
12 C Secondary_carbon, Ketone, CH-acidic CCC=O 1 952 957
13 C Secondary_carbon, Quaternary_carbon, Ketone CCC=O 1 952 957
14 O Ketone CCC=O 1 952 957
16 C Primary_carbon, Quaternary_carbon C 2 952 957
6 O Phenol O 1 953 954
7 C Secondary_carbon, Aromatic [nH]ccCCN 2 953 954
8 C Secondary_carbon [nH]ccCCN 2 953 954
9 C Secondary_carbon [nH]ccCCN 2 953 954
10 N Primary_aliph_amine [nH]ccCCN 2 953 954
11 C Aromatic [nH]ccCCN 2 953 954
12 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic [nH]ccCCN 2 953 954
0 C Primary_carbon, Tertiary_carbon CCC(=O)O 1 954 975
1 C Primary_carbon, Tertiary_carbon, Lactone, CH-acidic CCC(=O)O 1 954 975
10 O Ketone O 2 954 975
15 O Lactone, Heterocyclic CCC(=O)O 1 954 975
16 C Tertiary_carbon, Lactone CCC(=O)O 1 954 975
17 O Lactone CCC(=O)O 1 954 975
0 C Alkylarylether CO 1 955 1009
1 O Alkylarylether CO 1 955 1009
7 O Lactone, Oxoarene, Conjugated_double_bond O 2 955 1009
13 C Aromatic cco 3 955 1009
14 C Aromatic cco 3 955 1009
15 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic cco 3 955 1009
16 O Alkylarylether CO 4 955 1009
17 C Alkylarylether CO 4 955 1009
0 C Alkene, Conjugated_double_bond C=CC=O 1 957 961
1 C Tertiary_carbon, Alkene, Ketone, Conjugated_double_bond C=CC=O 1 957 961
7 C Quaternary_carbon, Hemiacetal CO 2 957 961
8 O Hemiacetal, Acetal_like, Heterocyclic, Sugar_pattern_2, Sugar_pattern_2_reducing CO 2 957 961
13 C Primary_carbon, Quaternary_carbon C 3 957 961
14 C Primary_carbon, Quaternary_carbon C 4 957 961
18 O Secondary_alcohol O 5 957 961
21 C Quaternary_carbon, Ketone, Conjugated_double_bond C=CC=O 1 957 961
22 O Ketone, Conjugated_double_bond C=CC=O 1 957 961
0 C Alkylarylether C 1 958 1015
20 C Alkylarylether C 2 958 1015
22 C Alkylarylether C 3 958 1015
18 C Carboxylic_ester CC(O)CO 1 959 972
19 C Secondary_alcohol, 1,2-Diol CC(O)CO 1 959 972
20 C Primary_alcohol, 1,2-Diol CC(O)CO 1 959 972
21 O Primary_alcohol, 1,2-Diol CC(O)CO 1 959 972
22 O Secondary_alcohol, 1,2-Diol CC(O)CO 1 959 972
0 C Primary_carbon, CH-acidic CC=O 1 960 988
1 C Primary_carbon, Carboxylic_ester CC=O 1 960 988
2 O Carboxylic_ester CC=O 1 960 988
17 C Primary_carbon, Carboxylic_ester CC=O 2 960 988
18 O Carboxylic_ester CC=O 2 960 988
19 C Primary_carbon, CH-acidic CC=O 2 960 988
21 C Primary_carbon, Carboxylic_ester CC=O 3 960 988
22 O Carboxylic_ester CC=O 3 960 988
23 C Primary_carbon, CH-acidic CC=O 3 960 988
0 C Aromatic cccc 1 961 1017
1 C Aromatic cccc 1 961 1017
2 C Aromatic, Conjugated_double_bond cccc 1 961 1017
5 C Aromatic, Conjugated_double_bond cccc 1 961 1017
7 O Ketone, Conjugated_double_bond O 2 961 1017
15 O Ketone, Conjugated_double_bond O 3 961 1017
16 O Phenol, 1,2-Diphenol O 4 961 1017
17 O Phenol, 1,2-Diphenol O 5 961 1017
0 C Primary_carbon CC=C(C)C 1 962 987
1 C Primary_carbon, Alkene CC=C(C)C 1 962 987
2 C Secondary_carbon, Alkene CC=C(C)C 1 962 987
3 C Secondary_carbon CC=C(C)C 1 962 987
14 C Alkene, Conjugated_double_bond C=CC(C)(C)O 2 962 987
15 C Alkene, Conjugated_double_bond C=CC(C)(C)O 2 962 987
16 C Primary_carbon, Alkylarylether C=CC(C)(C)O 2 962 987
17 C Primary_carbon C=CC(C)(C)O 2 962 987
18 C Primary_carbon C=CC(C)(C)O 2 962 987
19 O Alkylarylether, Heterocyclic C=CC(C)(C)O 2 962 987
27 O Phenol, 1,2-Diphenol O 3 962 987
29 O Phenol O 4 962 987
30 C Primary_carbon CC=C(C)C 1 962 987
0 C Alkylarylether C 1 963 1013
12 C Aromatic cco 2 963 1013
13 C Aromatic cco 2 963 1013
14 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic cco 2 963 1013
0 C Primary_carbon, Secondary_carbon CCCC 1 964 1002
1 C Primary_carbon, Secondary_carbon CCCC 1 964 1002
2 C Secondary_carbon CCCC 1 964 1002
3 C Secondary_carbon CCCC 1 964 1002
18 O Ketone, Conjugated_double_bond O 2 964 1002
19 C Secondary_carbon, Ketone, CH-acidic CCCC 3 964 1002
20 C Secondary_carbon CCCC 3 964 1002
21 C Primary_carbon, Secondary_carbon CCCC 3 964 1002
22 C Primary_carbon, Secondary_carbon CCCC 3 964 1002
28 C Alkylarylether C 4 964 1002
6 O Ketone O 1 965 1021
31 O Secondary_alcohol O 2 965 1021
32 O Secondary_alcohol O 3 965 1021
0 C Primary_carbon, Ketone, CH-acidic C 1 969 1008
2 O Ketone, Conjugated_double_bond O 2 969 1008
9 O Alkylarylether CO 3 969 1008
10 C Alkylarylether CO 3 969 1008
11 O Alkylarylether CO 4 969 1008
12 C Alkylarylether CO 4 969 1008
13 O Phenol O 5 969 1008
0 C Primary_carbon, Ketone, CH-acidic CC=O 1 971 1017
1 C Primary_carbon, Ketone CC=O 1 971 1017
2 O Ketone CC=O 1 971 1017
16 C Primary_carbon, Quaternary_carbon C 2 971 1017
22 O Carboxylic_ester CC(=O)O 3 971 1017
23 C Primary_carbon, Carboxylic_ester CC(=O)O 3 971 1017
24 O Carboxylic_ester CC(=O)O 3 971 1017
25 C Primary_carbon, CH-acidic CC(=O)O 3 971 1017
26 O Dialkylether, Heterocyclic, Epoxide O 4 971 1017
8 O Acetal, Acetal_like, Heterocyclic OCO 1 974 1014
9 C Acetal, Acetal_like OCO 1 974 1014
10 O Acetal, Acetal_like, Heterocyclic OCO 1 974 1014
12 C Alkene, Conjugated_double_bond CC(=O)O 2 974 1014
13 C Carboxylic_acid, Conjugated_double_bond CC(=O)O 2 974 1014
14 O Carboxylic_acid, Conjugated_double_bond CC(=O)O 2 974 1014
15 O Carboxylic_acid CC(=O)O 2 974 1014
2 C Quaternary_carbon, Alkene, Conjugated_double_bond C=CC(C)=O 1 975 1017
3 C Alkene, Ketone, Conjugated_double_bond C=CC(C)=O 1 975 1017
4 C Ketone, Conjugated_double_bond C=CC(C)=O 1 975 1017
5 O Ketone, Conjugated_double_bond C=CC(C)=O 1 975 1017
6 C Alkene, Ketone, Conjugated_double_bond C=CC(C)=O 1 975 1017
15 O Ketone O 2 975 1017
25 O Alkylarylether CO 1 977 978
26 C Alkylarylether CO 1 977 978
8 O Alkylarylether CO 1 979 986
9 C Alkylarylether CO 1 979 986
20 O Alkylarylether CO 2 979 986
21 C Alkylarylether CO 2 979 986
24 O Alkylarylether CO 3 979 986
25 C Alkylarylether CO 3 979 986
27 O Alkylarylether CO 4 979 986
28 C Alkylarylether CO 4 979 986
0 C Primary_carbon CC 1 980 1013
1 C Primary_carbon, Alkene CC 1 980 1013
4 C Tertiary_carbon, Alkene C=C(C)C 2 980 1013
5 C Primary_carbon, Secondary_carbon, Alkene C=C(C)C 2 980 1013
6 C Primary_carbon C=C(C)C 2 980 1013
7 C Secondary_carbon C=C(C)C 2 980 1013
13 O Lactam, Oxoarene, Conjugated_double_bond O 3 980 1013
17 N Primary_aliph_amine N 4 980 1013
0 C Primary_carbon, CH-acidic CC=O 1 981 1021
1 C Primary_carbon, Carboxylic_ester CC=O 1 981 1021
2 O Carboxylic_ester CC=O 1 981 1021
0 C Primary_carbon, CH-acidic CC(=O)O 1 983 1021
1 C Primary_carbon, Carboxylic_ester CC(=O)O 1 983 1021
2 O Carboxylic_ester CC(=O)O 1 983 1021
3 O Carboxylic_ester CC(=O)O 1 983 1021
28 O Ketone O 2 983 1021
35 O Carboxylic_ester CC(=O)O 3 983 1021
36 C Primary_carbon, Carboxylic_ester CC(=O)O 3 983 1021
37 O Carboxylic_ester CC(=O)O 3 983 1021
38 C Primary_carbon, CH-acidic CC(=O)O 3 983 1021
0 C Primary_carbon CC=C(C)C 1 984 990
1 C Primary_carbon, Alkene CC=C(C)C 1 984 990
2 C Alkene CC=C(C)C 1 984 990
3 C Alkylarylether CC=C(C)C 1 984 990
12 O Lactone, Oxoarene, Conjugated_double_bond O 2 984 990
16 O Phenol O 3 984 990
17 C Primary_carbon CC=C(C)C 1 984 990
0 C Alkylarylether CO 1 986 989
1 O Alkylarylether CO 1 986 989
19 O Alkylarylether CO 2 986 989
20 C Alkylarylether CO 2 986 989
0 C Primary_carbon CC=C(C)C 1 990 991
1 C Primary_carbon, Alkene CC=C(C)C 1 990 991
2 C Secondary_carbon, Alkene CC=C(C)C 1 990 991
3 C Secondary_carbon CC=C(C)C 1 990 991
18 C Primary_carbon CC=C(C)C 1 990 991
0 C Primary_carbon CC=C(C)C 1 991 1009
1 C Primary_carbon, Alkene CC=C(C)C 1 991 1009
2 C Secondary_carbon, Alkene CC=C(C)C 1 991 1009
3 C Secondary_carbon CC=C(C)C 1 991 1009
13 C Primary_carbon C 2 991 1009
16 O Phenol O 3 991 1009
17 O Alkylarylether CO 4 991 1009
18 C Alkylarylether CO 4 991 1009
19 C Primary_carbon CC=C(C)C 1 991 1009
0 C Primary_carbon CC=C(C)CO 1 993 995
1 C Primary_carbon, Alkene CC=C(C)CO 1 993 995
2 C Secondary_carbon, Alkene CC=C(C)CO 1 993 995
3 C Secondary_carbon CC=C(C)CO 1 993 995
9 C Oxoarene, Aromatic, Conjugated_double_bond Cc(o)cc=O 2 993 995
10 O Oxoarene, Conjugated_double_bond Cc(o)cc=O 2 993 995
11 C Aromatic, Conjugated_double_bond Cc(o)cc=O 2 993 995
12 C Primary_carbon, Aromatic, Conjugated_double_bond Cc(o)cc=O 2 993 995
13 C Primary_carbon Cc(o)cc=O 2 993 995
14 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic Cc(o)cc=O 2 993 995
17 O Alkylarylether, Heterocyclic CC=C(C)CO 1 993 995
18 C Alkylarylether CC=C(C)CO 1 993 995
0 C NA C=[N+](C)CC 1 995 1004
1 N Immonium, Heterocyclic, Conjugated_double_bond, Kation C=[N+](C)CC 1 995 1004
2 C Conjugated_double_bond C=[N+](C)CC 1 995 1004
5 C Secondary_carbon C=[N+](C)CC 1 995 1004
6 C Secondary_carbon C=[N+](C)CC 1 995 1004
13 O Acetal, Acetal_like, Heterocyclic OCO 2 995 1004
14 C Acetal, Acetal_like OCO 2 995 1004
15 O Acetal, Acetal_like, Heterocyclic OCO 2 995 1004
0 C Primary_carbon C=CC(C)(C)O 1 996 1004
1 C Primary_carbon, Alkylarylether C=CC(C)(C)O 1 996 1004
2 C Primary_carbon C=CC(C)(C)O 1 996 1004
3 C Alkene, Conjugated_double_bond C=CC(C)(C)O 1 996 1004
4 C Alkene, Conjugated_double_bond C=CC(C)(C)O 1 996 1004
8 C Aromatic, Conjugated_double_bond ccc(=O)o 2 996 1004
9 C Lactone, Aromatic, Conjugated_double_bond ccc(=O)o 2 996 1004
10 C Lactone, Oxoarene, Aromatic, Conjugated_double_bond ccc(=O)o 2 996 1004
11 O Lactone, Oxoarene, Conjugated_double_bond ccc(=O)o 2 996 1004
12 O Lactone, Hetero_O, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond ccc(=O)o 2 996 1004
16 O Alkylarylether, Heterocyclic C=CC(C)(C)O 1 996 1004
20 O Phenol, 1,2-Diphenol O 1 998 1001
6 O Phenol O 1 1001 1012
18 O Phenol, 1,2-Diphenol O 2 1001 1012
19 O Phenol, 1,2-Diphenol O 3 1001 1012
20 O Tertiary_alcohol O 4 1001 1012
0 C Alkylarylether CO 1 1004 1008
1 O Alkylarylether CO 1 1004 1008
8 O Alkylarylether CO 2 1004 1008
9 C Alkylarylether CO 2 1004 1008
10 O Alkylarylether CO 3 1004 1008
11 C Alkylarylether CO 3 1004 1008
12 O Phenol O 4 1004 1008
21 O Phenol, 1,2-Diphenol O 1 1006 1022
0 C NA CN 1 1008 1014
1 N Secondary_aliph_amine CN 1 1008 1014
0 C Primary_carbon, Tertiary_carbon CCCO 1 1012 1017
1 C Primary_carbon, Tertiary_carbon CCCO 1 1012 1017
2 C Tertiary_carbon, Enolether CCCO 1 1012 1017
3 O Enolether, Heterocyclic CCCO 1 1012 1017
9 O Ketone, Conjugated_double_bond O 2 1012 1017
17 C Primary_carbon, Quaternary_carbon C 3 1012 1017
7 O Phenol O 1 1015 1019
21 O Phenol O 2 1015 1019
Code 
comparison_table_add %>%
  kbl(escape = FALSE, format = "html", align = "l") %>%
  kable_styling(full_width = FALSE, position = "center", bootstrap_options = c("striped", "hover", "condensed"))
atom_idx atom_symbol matched_fg frag_smiles frag_id idx1 idx2
7 O Phenol O 1 11 2
8 O Phenol O 2 11 2
0 C Primary_carbon, Tertiary_carbon C 1 95 5
2 C Primary_carbon, Tertiary_carbon C 2 95 5
7 N Primary_aliph_amine, Alpha_aminoacid N 3 95 5
13 C Carboxylic_acid, Conjugated_double_bond O=CO 1 353 6
14 O Carboxylic_acid, Conjugated_double_bond O=CO 1 353 6
15 O Carboxylic_acid O=CO 1 353 6
3 O Ketone, Conjugated_double_bond O 1 415 7
10 Cl Arylchloride Cl 2 415 7
13 C Primary_carbon C 3 415 7
14 C Primary_carbon C 4 415 7
15 C Primary_carbon C 5 415 7
8 O Phenol O 1 11 8
0 C Primary_carbon C 1 11 9
0 C Aromatic cccc 1 83 10
1 C Aromatic cccc 1 83 10
2 C Aromatic cccc 1 83 10
5 C Aromatic cccc 1 83 10
9 O Lactone, Oxoarene, Conjugated_double_bond O 2 83 10
7 O Phenol, 1,2-Diphenol O 1 13 11
0 C Primary_carbon CC(C)=CCN 1 57 12
1 C Primary_carbon, Alkene CC(C)=CCN 1 57 12
2 C Alkene CC(C)=CCN 1 57 12
3 C NA CC(C)=CCN 1 57 12
4 N NA CC(C)=CCN 1 57 12
8 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nc[nH] 2 57 12
9 C Aromatic nc[nH] 2 57 12
10 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic nc[nH] 2 57 12
14 C Primary_carbon CC(C)=CCN 1 57 12
0 C Alkylarylether C 1 1004 13
9 C Alkylarylether C 2 1004 13
11 C Alkylarylether C 3 1004 13
12 O Phenol O 4 1004 13
2 C Primary_carbon, Tertiary_carbon C 1 95 14
5 O Carboxylic_acid, Alpha_aminoacid O 2 95 14
7 N Primary_aliph_amine, Alpha_aminoacid N 3 95 14
9 O Lactam O 1 608 15
18 Br Arylbromide Br 2 608 15
7 N Primary_arom_amine N 1 522 16
8 O Lactam O 1 32 18
8 Cl Arylchloride Cl 1 556 19
9 Cl Arylchloride Cl 2 556 19
10 N Primary_aliph_amine N 3 556 19
0 C Alkene C 1 943 20
5 C Primary_carbon C 2 943 20
13 C Primary_carbon, Quaternary_carbon C 3 943 20
14 O Dialkylether, Heterocyclic, Epoxide O 4 943 20
12 O Primary_alcohol O 1 972 21
13 O Secondary_alcohol, 1,2-Diol O 2 972 21
14 O Secondary_alcohol, 1,2-Diol O 3 972 21
0 C Primary_carbon, Secondary_carbon C 1 23 22
15 O Carboxylic_acid O 1 29 23
16 O Carboxylic_acid O 2 29 23
20 Cl Arylchloride Cl 3 29 23
0 C Primary_carbon C 1 30 24
19 Cl Arylchloride Cl 2 30 24
20 O Secondary_alcohol O 3 30 24
0 C Primary_carbon C 1 219 27
7 N Tertiary_mixed_amine CNC 2 219 27
8 C NA CNC 2 219 27
9 C NA CNC 2 219 27
12 O Urethan O 3 219 27
15 O Carboxylic_acid O 1 29 28
16 O Carboxylic_acid O 2 29 28
20 O Secondary_alcohol O 1 30 29
0 C Primary_carbon, Secondary_carbon CC 1 278 30
1 C Primary_carbon, Secondary_carbon CC 1 278 30
7 C Aromatic c1ccccc1 2 278 30
8 C Aromatic c1ccccc1 2 278 30
9 C Aromatic c1ccccc1 2 278 30
10 C Aromatic c1ccccc1 2 278 30
11 C Aromatic c1ccccc1 2 278 30
12 C Aromatic c1ccccc1 2 278 30
20 C Alkylfluoride, Trifluoromethyl FC(F)F 3 278 30
21 F Alkylfluoride, Trifluoromethyl FC(F)F 3 278 30
22 F Alkylfluoride, Trifluoromethyl FC(F)F 3 278 30
23 F Alkylfluoride, Trifluoromethyl FC(F)F 3 278 30
24 F Arylfluoride F 4 278 30
9 Cl Arylchloride Cl 1 35 32
0 C Primary_carbon CC 1 868 33
1 C Primary_carbon CC 1 868 33
11 O Urea, Oxoarene, Conjugated_double_bond O 2 868 33
12 Cl Arylchloride Cl 3 868 33
13 Cl Arylchloride Cl 4 868 33
6 O Phenol O 1 55 34
10 O Carboxylic_acid O 2 55 34
11 O Carboxylic_acid O 3 55 34
9 N Primary_arom_amine N 1 38 35
0 C Primary_carbon C 1 45 38
0 C Primary_carbon, Tertiary_carbon C 1 911 39
6 C Primary_carbon, Quaternary_carbon C 2 911 39
7 C Primary_carbon, Quaternary_carbon C 3 911 39
11 O Carboxylic_ester, Conjugated_double_bond O 4 911 39
18 O Phenol O 5 911 39
9 C Nitrile, Conjugated_tripple_bond C#N 1 43 40
10 N Nitrile, Conjugated_tripple_bond C#N 1 43 40
9 C Nitrile, Conjugated_tripple_bond C#N 1 43 41
10 N Nitrile, Conjugated_tripple_bond C#N 1 43 41
0 C Primary_carbon C=C(C)C 1 57 42
1 C Primary_carbon, Alkene C=C(C)C 1 57 42
2 C Alkene C=C(C)C 1 57 42
14 C Primary_carbon C=C(C)C 1 57 42
0 C Alkylarylether CO 1 44 43
1 O Alkylarylether CO 1 44 43
0 C Primary_carbon C 1 45 44
10 O Aldehyde, Conjugated_double_bond O 1 50 45
6 Cl Arylchloride Cl 1 451 46
9 O Urethan, Oxoarene, Conjugated_double_bond O 2 451 46
4 C Aromatic cc[nH] 1 49 47
5 C Aromatic cc[nH] 1 49 47
6 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic cc[nH] 1 49 47
9 C Carboxylic_acid, Conjugated_double_bond O=CO 2 49 47
10 O Carboxylic_acid, Conjugated_double_bond O=CO 2 49 47
11 O Carboxylic_acid O=CO 2 49 47
10 O Primary_alcohol O 1 51 50
10 O Carboxylic_acid, Conjugated_double_bond O 1 52 51
8 C Secondary_carbon, Primary_alcohol CO 1 71 52
9 O Primary_alcohol CO 1 71 52
7 C Secondary_carbon CCO 1 71 53
8 C Secondary_carbon, Primary_alcohol CCO 1 71 53
9 O Primary_alcohol CCO 1 71 53
6 O Phenol O 1 55 54
8 C Secondary_carbon CC(=O)O 2 55 54
9 C Secondary_carbon, Carboxylic_acid CC(=O)O 2 55 54
10 O Carboxylic_acid CC(=O)O 2 55 54
11 O Carboxylic_acid CC(=O)O 2 55 54
0 C Primary_carbon C 1 56 55
15 C Alkylarylether C 2 56 55
11 N Primary_aliph_amine N 1 635 56
0 C Secondary_carbon C1CCCC1 1 463 57
1 C Secondary_carbon C1CCCC1 1 463 57
2 C Secondary_carbon C1CCCC1 1 463 57
3 C Secondary_carbon C1CCCC1 1 463 57
4 C Secondary_carbon C1CCCC1 1 463 57
13 Cl Arylchloride Cl 1 69 58
14 Cl Arylchloride Cl 2 69 58
13 O Primary_alcohol O 1 62 60
19 O Secondary_alcohol O 1 63 61
2 O Secondary_amide O 1 600 62
15 I Aryliodide I 2 600 62
16 O Alkylarylether CO 3 600 62
17 C Alkylarylether CO 3 600 62
0 C Aromatic c1ccccc1 1 67 66
1 C Aromatic c1ccccc1 1 67 66
2 C Aromatic c1ccccc1 1 67 66
3 C Secondary_carbon, Aromatic c1ccccc1 1 67 66
4 C Aromatic c1ccccc1 1 67 66
5 C Aromatic c1ccccc1 1 67 66
6 C Secondary_carbon CC(=O)O 1 69 68
7 C Secondary_carbon, Carboxylic_acid CC(=O)O 1 69 68
8 O Carboxylic_acid CC(=O)O 1 69 68
9 O Carboxylic_acid CC(=O)O 1 69 68
13 Cl Arylchloride Cl 2 69 68
14 Cl Arylchloride Cl 3 69 68
12 O Phenol O 1 653 70
13 N Primary_aliph_amine N 2 653 70
7 O Carboxylic_acid O 1 72 71
13 Cl Arylchloride Cl 2 72 71
14 Cl Arylchloride Cl 3 72 71
11 Cl Arylchloride Cl 1 73 72
10 Cl Arylchloride Cl 1 74 73
11 Cl Arylchloride Cl 2 74 73
0 C Primary_carbon C 1 75 74
13 Cl Arylchloride Cl 1 76 75
14 Cl Arylchloride Cl 2 76 75
13 Cl Arylchloride Cl 1 78 77
9 N Primary_aliph_amine N 1 377 78
10 C Secondary_carbon CCC 1 81 80
11 C Secondary_carbon CCC 1 81 80
12 C Secondary_carbon, Quaternary_carbon CCC 1 81 80
12 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic [nH]n 1 553 81
13 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic [nH]n 1 553 81
15 O Ketone, Conjugated_double_bond O 2 553 81
0 C Primary_carbon C 1 119 83
12 N Primary_arom_amine N 2 119 83
6 O Phenol, 1,2-Diphenol O 1 86 84
0 C Alkylarylether C 1 90 86
0 C Alkylarylether CO 1 1014 87
1 O Alkylarylether CO 1 1014 87
8 O Phenol O 2 1014 87
4 C Carboxylic_acid, Conjugated_double_bond O=CO 1 481 88
5 O Carboxylic_acid, Conjugated_double_bond O=CO 1 481 88
6 O Carboxylic_acid O=CO 1 481 88
9 C Carboxylic_acid, Conjugated_double_bond O=CO 2 481 88
10 O Carboxylic_acid, Conjugated_double_bond O=CO 2 481 88
11 O Carboxylic_acid O=CO 2 481 88
12 O Phenol O 3 481 88
0 C Primary_carbon, Secondary_carbon CCC 1 230 89
1 C Primary_carbon, Secondary_carbon CCC 1 230 89
2 C Secondary_carbon CCC 1 230 89
6 C Primary_carbon C 2 230 89
9 N NA CCN 3 230 89
10 C Primary_carbon CCN 3 230 89
11 C Primary_carbon CCN 3 230 89
14 O Imidoacid_cyclic, Phenol O 4 230 89
8 N Primary_amide N 1 99 90
0 C Primary_carbon, Tertiary_carbon CCC 1 95 91
1 C Primary_carbon, Tertiary_carbon CCC 1 95 91
2 C Primary_carbon, Tertiary_carbon CCC 1 95 91
7 N Primary_aliph_amine, Alpha_aminoacid N 2 95 91
2 O Carboxylic_acid O 1 94 93
3 O Carboxylic_acid O 2 94 93
7 O Carboxylic_acid O 3 94 93
8 O Carboxylic_acid O 4 94 93
9 C Carboxylic_acid, Alpha_hydroxyacid O=CO 5 94 93
10 O Carboxylic_acid, Alpha_hydroxyacid O=CO 5 94 93
11 O Carboxylic_acid, Alpha_hydroxyacid O=CO 5 94 93
12 O Tertiary_alcohol, Alpha_hydroxyacid O 6 94 93
7 N Primary_aliph_amine, Alpha_aminoacid N 1 95 94
3 O Carboxylic_acid, Alpha_hydroxyacid O 1 1016 95
4 O Carboxylic_acid, Alpha_hydroxyacid O 2 1016 95
5 O Secondary_alcohol, 1,2-Diol, Alpha_hydroxyacid O 3 1016 95
9 O Secondary_alcohol, 1,2-Diol, Alpha_hydroxyacid O 4 1016 95
0 C Primary_carbon C 1 97 96
0 C Primary_carbon, Secondary_carbon C 1 98 97
6 C Tertiary_amide C 2 98 97
0 C Primary_carbon C 1 116 98
4 C Primary_carbon C 2 116 98
8 N Amidine N 1 380 100
9 N Primary_arom_amine N 2 380 100
0 C Primary_carbon, Secondary_carbon C 1 102 101
0 C Primary_carbon, Secondary_carbon C 1 103 102
0 C Primary_carbon, Secondary_carbon C 1 104 103
0 C Primary_carbon, Secondary_carbon C 1 105 104
0 C Primary_carbon, Secondary_carbon C 1 106 105
0 C Primary_carbon, Secondary_carbon C 1 107 106
0 C Primary_carbon, Secondary_carbon C 1 108 107
0 C Primary_carbon, Secondary_carbon C 1 109 108
0 C Primary_carbon, Secondary_carbon C 1 110 109
0 C Primary_carbon, Secondary_carbon C 1 111 110
0 C Primary_carbon, Secondary_carbon C 1 112 111
0 C Primary_carbon, Secondary_carbon C 1 113 112
0 C Primary_carbon, Secondary_carbon C 1 114 113
0 C Primary_carbon, Secondary_carbon C 1 115 114
0 C Secondary_carbon C1CNC1 1 361 116
1 C Secondary_carbon C1CNC1 1 361 116
2 N Secondary_aliph_amine, Alpha_aminoacid, Heterocyclic C1CNC1 1 361 116
3 C Secondary_carbon, Alpha_aminoacid C1CNC1 1 361 116
6 O Carboxylic_acid, Alpha_aminoacid O 2 361 116
0 C Primary_carbon CCO 1 121 117
1 C Primary_carbon, Acetal CCO 1 121 117
2 O Acetal, Acetal_like CCO 1 121 117
12 O Acetal, Acetal_like CCO 2 121 117
13 C Primary_carbon, Acetal CCO 2 121 117
14 C Primary_carbon CCO 2 121 117
0 C Alkene C 1 943 118
5 C Primary_carbon C 2 943 118
12 C Primary_carbon, Quaternary_carbon C 3 943 118
13 C Primary_carbon, Quaternary_carbon C 4 943 118
14 O Dialkylether, Heterocyclic, Epoxide O 5 943 118
0 C Alkylarylether CO 1 955 119
1 O Alkylarylether CO 1 955 119
13 C Aromatic cco 2 955 119
14 C Aromatic cco 2 955 119
15 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic cco 2 955 119
16 O Alkylarylether CO 3 955 119
17 C Alkylarylether CO 3 955 119
0 C Alkylarylether CO 1 349 120
1 O Alkylarylether CO 1 349 120
9 C Secondary_carbon CCNC 2 349 120
10 C Secondary_carbon CCNC 2 349 120
11 N Secondary_aliph_amine, Heterocyclic CCNC 2 349 120
12 C NA CCNC 2 349 120
0 C Primary_carbon, Secondary_carbon C 1 202 121
3 C Primary_carbon, Secondary_carbon CC 2 202 121
4 C Primary_carbon, Secondary_carbon CC 2 202 121
10 C Primary_carbon C 3 202 121
12 C Primary_carbon C 4 202 121
14 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 5 202 121
15 O Anion O=[NH+][O-] 5 202 121
16 O Conjugated_double_bond O=[NH+][O-] 5 202 121
17 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 6 202 121
18 O Anion O=[NH+][O-] 6 202 121
19 O Conjugated_double_bond O=[NH+][O-] 6 202 121
0 C Primary_carbon, Secondary_carbon C 1 124 122
10 C Primary_carbon, Secondary_carbon C 2 124 122
15 C Primary_carbon, Secondary_carbon C 3 124 122
20 C Primary_carbon, Secondary_carbon C 4 124 122
9 O Carboxylic_acid O 1 913 123
14 C Secondary_carbon, Tertiary_carbon CC1C=CCC1 2 913 123
15 C Secondary_carbon, Tertiary_carbon CC1C=CCC1 2 913 123
16 C Tertiary_carbon, Alkene CC1C=CCC1 2 913 123
17 C Secondary_carbon, Alkene CC1C=CCC1 2 913 123
18 C Secondary_carbon CC1C=CCC1 2 913 123
19 C Secondary_carbon, Tertiary_carbon CC1C=CCC1 2 913 123
7 O Carboxylic_ester CC(=O)O 1 363 124
8 C Primary_carbon, Carboxylic_ester CC(=O)O 1 363 124
9 O Carboxylic_ester CC(=O)O 1 363 124
10 C Primary_carbon, CH-acidic CC(=O)O 1 363 124
0 C Primary_carbon, Quaternary_carbon C 1 496 125
7 C Primary_carbon, Quaternary_carbon C 2 496 125
11 O Dialkylether, Heterocyclic O 3 496 125
0 C Primary_carbon, Tertiary_carbon C 1 409 126
26 O Secondary_alcohol O 2 409 126
27 Cl Alkylchloride Cl 3 409 126
0 C Primary_carbon, Secondary_carbon CCC 1 176 129
1 C Primary_carbon, Secondary_carbon CCC 1 176 129
2 C Secondary_carbon CCC 1 176 129
0 C Primary_carbon C 1 137 133
6 C Primary_carbon C 2 137 133
11 O Dialkylether CO 3 137 133
12 C Dialkylether CO 3 137 133
15 C Alkylchloride CCl 4 137 133
16 Cl Alkylchloride CCl 4 137 133
0 C Primary_carbon, Secondary_carbon CCCCC 1 202 134
1 C Primary_carbon, Secondary_carbon CCCCC 1 202 134
2 C Secondary_carbon CCCCC 1 202 134
3 C Primary_carbon, Secondary_carbon CCCCC 1 202 134
4 C Primary_carbon, Secondary_carbon CCCCC 1 202 134
12 C Primary_carbon C 2 202 134
14 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 3 202 134
15 O Anion O=[NH+][O-] 3 202 134
16 O Conjugated_double_bond O=[NH+][O-] 3 202 134
17 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 4 202 134
18 O Anion O=[NH+][O-] 4 202 134
19 O Conjugated_double_bond O=[NH+][O-] 4 202 134
0 C Primary_carbon, Secondary_carbon CC 1 148 135
1 C Primary_carbon, Secondary_carbon CC 1 148 135
5 C Quaternary_carbon, Nitrile C#N 2 148 135
6 N Nitrile C#N 2 148 135
0 C Primary_carbon, Secondary_carbon C 1 196 137
11 C Primary_carbon C 2 196 137
21 O Carboxylic_ester CO 1 238 138
22 C Carboxylic_ester CO 1 238 138
0 C Secondary_amide CN 1 265 139
1 N Secondary_amide CN 1 265 139
3 O Secondary_amide O 2 265 139
7 O NA O 3 265 139
0 C Primary_carbon, Secondary_carbon CCCS 1 209 140
1 C Primary_carbon, Secondary_carbon CCCS 1 209 140
2 C Secondary_carbon CCCS 1 209 140
3 S NA CCCS 1 209 140
16 Cl Arylchloride Cl 2 209 140
17 Br Arylbromide Br 3 209 140
4 N NA N 1 147 143
2 C Carboxylic_acid, Alpha_hydroxyacid O=CO 1 1016 145
3 O Carboxylic_acid, Alpha_hydroxyacid O=CO 1 1016 145
4 O Carboxylic_acid, Alpha_hydroxyacid O=CO 1 1016 145
9 O Secondary_alcohol, 1,2-Diol, Alpha_hydroxyacid O 2 1016 145
6 Cl Arylchloride Cl 1 170 146
7 Cl Arylchloride Cl 2 170 146
12 C Aromatic, Conjugated_double_bond ccc(c)F 3 170 146
13 C Arylfluoride, Aromatic ccc(c)F 3 170 146
14 C Aromatic ccc(c)F 3 170 146
15 C Aromatic ccc(c)F 3 170 146
19 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 4 170 146
20 C Aromatic c1ncnn1 4 170 146
21 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 4 170 146
22 C Aromatic c1ncnn1 4 170 146
23 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 4 170 146
24 F Arylfluoride ccc(c)F 3 170 146
0 C Primary_carbon, Secondary_carbon CC 1 167 147
1 C Primary_carbon, Secondary_carbon CC 1 167 147
8 C Primary_carbon C 2 167 147
9 S NA CCCS 3 167 147
10 C Secondary_carbon CCCS 3 167 147
11 C Primary_carbon, Secondary_carbon CCCS 3 167 147
12 C Primary_carbon, Secondary_carbon CCCS 3 167 147
17 Cl Arylchloride Cl 1 172 148
19 O Tertiary_alcohol O 2 172 148
0 C Primary_carbon, Secondary_carbon CCCC 1 230 150
1 C Primary_carbon, Secondary_carbon CCCC 1 230 150
2 C Secondary_carbon CCCC 1 230 150
3 C Secondary_carbon CCCC 1 230 150
6 C Primary_carbon C 2 230 150
9 N NA CCN 3 230 150
10 C Primary_carbon CCN 3 230 150
11 C Primary_carbon CCN 3 230 150
14 O Imidoacid_cyclic, Phenol O 4 230 150
0 C Primary_carbon C 1 203 154
4 S NA S 2 203 154
7 C Primary_carbon C 3 203 154
12 C Aromatic ccc(c)Cl 4 203 154
13 C Aromatic ccc(c)Cl 4 203 154
14 C Arylchloride, Aromatic ccc(c)Cl 4 203 154
15 C Aromatic ccc(c)Cl 4 203 154
20 Cl Arylchloride ccc(c)Cl 4 203 154
8 N Tertiary_aliph_amine, Heterocyclic C1CCNC1 1 552 155
9 C Secondary_carbon C1CCNC1 1 552 155
10 C Secondary_carbon C1CCNC1 1 552 155
11 C Secondary_carbon C1CCNC1 1 552 155
12 C Secondary_carbon C1CCNC1 1 552 155
22 Cl Arylchloride Cl 2 552 155
23 Cl Arylchloride Cl 3 552 155
0 C NA CCN(C)C 1 456 157
1 N Tertiary_aliph_amine CCN(C)C 1 456 157
2 C NA CCN(C)C 1 456 157
3 C Secondary_carbon CCN(C)C 1 456 157
4 C Secondary_carbon CCN(C)C 1 456 157
13 F Arylfluoride F 2 456 157
15 C Aromatic ccc(c)C#N 3 456 157
16 C Aromatic, Conjugated_tripple_bond ccc(c)C#N 3 456 157
17 C Aromatic, Conjugated_tripple_bond ccc(c)C#N 3 456 157
18 C Aromatic, Conjugated_tripple_bond ccc(c)C#N 3 456 157
22 C Nitrile, Conjugated_tripple_bond ccc(c)C#N 3 456 157
23 N Nitrile, Conjugated_tripple_bond ccc(c)C#N 3 456 157
9 C Urethan CN(C)C=O 1 206 158
10 O Urethan CN(C)C=O 1 206 158
11 N Urethan CN(C)C=O 1 206 158
12 C NA CN(C)C=O 1 206 158
13 C NA CN(C)C=O 1 206 158
16 C NA C 2 206 158
0 C Primary_carbon CCNCC 1 207 162
1 C Primary_carbon CCNCC 1 207 162
2 N NA CCNCC 1 207 162
3 C Primary_carbon CCNCC 1 207 162
4 C Primary_carbon CCNCC 1 207 162
0 C Primary_carbon C 1 197 163
3 C Carboxylic_ester, Conjugated_double_bond COC=O 2 197 163
4 O Carboxylic_ester, Conjugated_double_bond COC=O 2 197 163
5 O Carboxylic_ester COC=O 2 197 163
6 C Carboxylic_ester COC=O 2 197 163
0 C Secondary_amide CN 1 265 167
1 N Secondary_amide CN 1 265 167
3 O Secondary_amide O 2 265 167
10 O NA CO 3 265 167
11 C NA CO 3 265 167
0 C Primary_carbon C 1 243 168
8 O Ketone, Conjugated_double_bond O 2 243 168
11 C Primary_carbon C 3 243 168
16 O Alkylarylether CO 4 243 168
17 C Alkylarylether CO 4 243 168
18 Br Arylbromide Br 5 243 168
19 O Alkylarylether CO 6 243 168
20 C Alkylarylether CO 6 243 168
21 O Alkylarylether CO 7 243 168
22 C Alkylarylether CO 7 243 168
23 O Alkylarylether CO 8 243 168
24 C Alkylarylether CO 8 243 168
0 C Primary_carbon, Quaternary_carbon C 1 177 169
2 C Primary_carbon, Quaternary_carbon C 2 177 169
3 C Primary_carbon, Quaternary_carbon C 3 177 169
20 O Tertiary_alcohol O 4 177 169
0 C Primary_carbon C 1 659 170
9 C Primary_carbon C 2 659 170
19 S Conjugated_double_bond NO[SH]=O 3 659 170
20 O Conjugated_double_bond NO[SH]=O 3 659 170
21 O NA NO[SH]=O 3 659 170
22 N NA NO[SH]=O 3 659 170
23 Cl Arylchloride Cl 4 659 170
2 C Primary_carbon, Tertiary_carbon C 1 311 173
6 C Primary_carbon C 2 311 173
10 O Urethan CNC(=O)O 3 311 173
11 C Urethan CNC(=O)O 3 311 173
12 O Urethan CNC(=O)O 3 311 173
13 N Urethan CNC(=O)O 3 311 173
14 C NA CNC(=O)O 3 311 173
2 C Primary_carbon, Quaternary_carbon C 1 175 174
0 C NA CNC(=O)O 1 302 176
1 N Urethan CNC(=O)O 1 302 176
2 C Urethan CNC(=O)O 1 302 176
3 O Urethan CNC(=O)O 1 302 176
4 O Urethan CNC(=O)O 1 302 176
14 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 1 200 177
15 C Aromatic c1ncnn1 1 200 177
16 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 1 200 177
17 C Aromatic c1ncnn1 1 200 177
18 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ncnn1 1 200 177
8 O Carboxylic_acid O 1 589 178
10 C Quaternary_carbon CN 2 589 178
11 N Primary_aliph_amine CN 2 589 178
6 O Halogen_acetal_like, Acetal_like OC(F)(F)F 1 737 179
7 C Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 1 737 179
8 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 1 737 179
9 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 1 737 179
10 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 1 737 179
13 N Primary_arom_amine, Isothiourea N 2 737 179
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 181
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 181
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 181
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 181
10 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N 2 782 181
11 C Thioamide, Conjugated_double_bond NC=S 3 782 181
12 S Thioamide, Conjugated_double_bond NC=S 3 782 181
13 N Thioamide NC=S 3 782 181
17 O Phenol O 4 782 181
18 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 181
19 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 181
20 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 181
21 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 181
5 O Ketone O 1 215 183
19 Cl Arylchloride Cl 2 215 183
16 C Secondary_carbon, Tertiary_carbon C1CCOCC1 1 213 184
17 C Secondary_carbon, Tertiary_carbon C1CCOCC1 1 213 184
18 C Secondary_carbon, Dialkylether C1CCOCC1 1 213 184
19 O Dialkylether, Heterocyclic C1CCOCC1 1 213 184
20 C Secondary_carbon, Dialkylether C1CCOCC1 1 213 184
21 C Secondary_carbon, Tertiary_carbon C1CCOCC1 1 213 184
15 Cl Arylchloride Cl 1 639 186
16 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 2 639 186
17 O Anion O=[NH+][O-] 2 639 186
18 O Conjugated_double_bond O=[NH+][O-] 2 639 186
0 C Primary_carbon C 1 247 187
4 C Primary_carbon C 2 247 187
23 O Carboxylic_ester OC1COC1 3 247 187
24 C Carboxylic_ester OC1COC1 3 247 187
25 C Dialkylether OC1COC1 3 247 187
26 O Dialkylether, Heterocyclic OC1COC1 3 247 187
27 C Dialkylether OC1COC1 3 247 187
14 S NA S 1 190 189
2 N NA CNC(=O)ON 1 222 190
3 O NA CNC(=O)ON 1 222 190
4 C NA CNC(=O)ON 1 222 190
5 O NA CNC(=O)ON 1 222 190
6 N NA CNC(=O)ON 1 222 190
7 C NA CNC(=O)ON 1 222 190
11 C Dialkylthioether C 2 222 190
7 O NA O 1 265 191
0 C Primary_carbon, Secondary_carbon C 1 196 193
18 Cl Alkylchloride Cl 2 196 193
0 C Primary_carbon, Secondary_carbon C 1 196 194
11 C Primary_carbon C 2 196 194
12 C Dialkylether COC 3 196 194
13 O Dialkylether COC 3 196 194
14 C Dialkylether COC 3 196 194
0 C Primary_carbon, Secondary_carbon C 1 202 196
4 C Primary_carbon, Secondary_carbon C 2 202 196
10 C Primary_carbon C 3 202 196
12 C Primary_carbon C 4 202 196
14 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 5 202 196
15 O Anion O=[NH+][O-] 5 202 196
16 O Conjugated_double_bond O=[NH+][O-] 5 202 196
17 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 6 202 196
18 O Anion O=[NH+][O-] 6 202 196
19 O Conjugated_double_bond O=[NH+][O-] 6 202 196
0 C Primary_carbon C 1 294 197
5 S NA S 2 294 197
0 C NA CCNC 1 521 198
1 N Secondary_aliph_amine CCNC 1 521 198
2 C Secondary_carbon CCNC 1 521 198
3 C Secondary_carbon CCNC 1 521 198
7 C Aromatic cccc 2 521 198
8 C Aromatic cccc 2 521 198
9 C Aromatic cccc 2 521 198
10 C Aromatic cccc 2 521 198
15 C Aromatic cccc 3 521 198
16 C Aromatic cccc 3 521 198
17 C Aromatic cccc 3 521 198
18 C Aromatic cccc 3 521 198
3 C Primary_carbon, Tertiary_carbon C 1 329 200
10 O Urethan CNC(=O)O 2 329 200
11 C Urethan CNC(=O)O 2 329 200
12 O Urethan CNC(=O)O 2 329 200
13 N Urethan CNC(=O)O 2 329 200
14 C NA CNC(=O)O 2 329 200
6 C Primary_carbon C 1 311 201
10 O Urethan CNC(=O)O 2 311 201
11 C Urethan CNC(=O)O 2 311 201
12 O Urethan CNC(=O)O 2 311 201
13 N Urethan CNC(=O)O 2 311 201
14 C NA CNC(=O)O 2 311 201
0 C NA CNC 1 289 202
1 N Urea CNC 1 289 202
2 C NA CNC 1 289 202
4 O Urea O 2 289 202
13 F Alkylfluoride, Trifluoromethyl F 3 289 202
14 F Alkylfluoride, Trifluoromethyl F 4 289 202
15 F Alkylfluoride, Trifluoromethyl F 5 289 202
0 C Primary_carbon, Secondary_carbon CCC 1 230 206
1 C Primary_carbon, Secondary_carbon CCC 1 230 206
2 C Secondary_carbon CCC 1 230 206
11 C Primary_carbon C 2 230 206
0 C Primary_carbon, Secondary_carbon CCCC 1 230 207
1 C Primary_carbon, Secondary_carbon CCCC 1 230 207
2 C Secondary_carbon CCCC 1 230 207
3 C Secondary_carbon CCCC 1 230 207
0 C Aromatic cccc 1 406 208
1 C Aromatic cccc 1 406 208
2 C Aromatic, Conjugated_double_bond cccc 1 406 208
5 C Aromatic, Conjugated_double_bond cccc 1 406 208
15 Cl Arylchloride Cl 2 406 208
16 N Primary_arom_amine N 3 406 208
0 C Primary_carbon CC(C)OC=O 1 236 209
1 C Primary_carbon, Carboxylic_ester CC(C)OC=O 1 236 209
2 C Primary_carbon CC(C)OC=O 1 236 209
3 O Carboxylic_ester CC(C)OC=O 1 236 209
4 C Carboxylic_ester, Conjugated_double_bond CC(C)OC=O 1 236 209
5 O Carboxylic_ester, Conjugated_double_bond CC(C)OC=O 1 236 209
14 S NA S 2 236 209
15 N NA N 3 236 209
0 C Primary_carbon C 1 294 210
8 O NA CO 2 294 210
9 C NA CO 2 294 210
0 C Primary_carbon CCO 1 259 211
1 C Primary_carbon, Alkylarylether CCO 1 259 211
2 O Alkylarylether CCO 1 259 211
9 O Alkylarylether CCO 2 259 211
10 C Primary_carbon, Alkylarylether CCO 2 259 211
11 C Primary_carbon CCO 2 259 211
0 C Primary_carbon CNC(C)C 1 731 214
1 C Primary_carbon CNC(C)C 1 731 214
2 C Primary_carbon CNC(C)C 1 731 214
3 N Secondary_aliph_amine, 1,2-Aminoalcohol CNC(C)C 1 731 214
4 C 1,2-Aminoalcohol CNC(C)C 1 731 214
16 C NA C 2 731 214
17 O Secondary_alcohol, 1,2-Aminoalcohol O 3 731 214
19 O Secondary_alcohol O 1 273 215
6 C Primary_carbon C 1 309 219
0 C Primary_carbon, Secondary_carbon C 1 258 220
7 C Primary_carbon, Secondary_carbon CC 2 258 220
8 C Primary_carbon, Secondary_carbon CC 2 258 220
2 C Primary_carbon C 1 322 222
17 C Carboxylic_ester, Conjugated_double_bond COC=O 1 245 225
18 O Carboxylic_ester, Conjugated_double_bond COC=O 1 245 225
19 O Carboxylic_ester COC=O 1 245 225
20 C Carboxylic_ester COC=O 1 245 225
7 C Aromatic c1ccccc1 1 531 227
8 C Aromatic c1ccccc1 1 531 227
9 C Aromatic c1ccccc1 1 531 227
10 C Aromatic c1ccccc1 1 531 227
11 C Aromatic c1ccccc1 1 531 227
12 C Aromatic c1ccccc1 1 531 227
14 O NA O 2 531 227
17 O Urea O 3 531 227
0 C NA CN 1 336 228
1 N NA CN 1 336 228
3 O NA O 2 336 228
11 C Tertiary_amide C 3 336 228
12 S NA CS 4 336 228
13 C NA CS 4 336 228
5 Cl Alkylchloride Cl 1 482 229
13 Br Arylbromide Br 2 482 229
0 C NA C 1 356 230
5 O Lactam, Oxoarene, Conjugated_double_bond O 2 356 230
7 C NA C 3 356 230
9 O Urea, Oxoarene, Conjugated_double_bond O 4 356 230
10 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond [nH]cn 5 356 230
11 C Aromatic [nH]cn 5 356 230
12 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic [nH]cn 5 356 230
12 C Primary_alcohol CO 1 847 234
13 O Primary_alcohol CO 1 847 234
15 O Secondary_alcohol, 1,2-Diol O 2 847 234
16 O Secondary_alcohol, 1,2-Diol O 3 847 234
18 Cl Arylchloride Cl 4 847 234
19 Cl Arylchloride Cl 5 847 234
0 C Primary_carbon C 1 276 236
4 C Primary_carbon C 2 276 236
10 C Urethan CNC=O 3 276 236
11 O Urethan CNC=O 3 276 236
12 N Urethan CNC=O 3 276 236
13 C NA CNC=O 3 276 236
0 C Primary_carbon C 1 934 238
8 C Carboxylic_acid, Conjugated_double_bond O=CO 2 934 238
9 O Carboxylic_acid, Conjugated_double_bond O=CO 2 934 238
10 O Carboxylic_acid O=CO 2 934 238
11 O Phenol O 3 934 238
14 O Carboxylic_ester, Conjugated_double_bond O 4 934 238
21 C Primary_carbon C 5 934 238
23 O Alkylarylether CO 6 934 238
24 C Alkylarylether CO 6 934 238
25 O Alkylarylether CO 7 934 238
26 C Alkylarylether CO 7 934 238
11 Br Arylbromide Br 1 295 239
0 C Primary_carbon C 1 425 240
12 O Carboxylic_acid O 2 425 240
13 O Carboxylic_acid O 3 425 240
23 Cl Arylchloride Cl 4 425 240
6 Cl Arylchloride Cl 1 877 242
7 Cl Arylchloride Cl 2 877 242
10 N Primary_arom_amine N 3 877 242
13 N Primary_arom_amine N 4 877 242
16 O Phenol O 1 935 243
17 O Alkylarylether OCCCl 1 256 245
18 C Alkylarylether OCCCl 1 256 245
19 C Alkylchloride OCCCl 1 256 245
20 Cl Alkylchloride OCCCl 1 256 245
0 C Primary_carbon C 1 294 246
5 S NA S 2 294 246
12 O Carboxylic_ester CO 3 294 246
13 C Carboxylic_ester CO 3 294 246
0 C Alkylarylether, Imidolactone CO 1 264 247
1 O Alkylarylether, Imidolactone CO 1 264 247
24 C Carboxylic_ester C 2 264 247
25 C NA CNS(C)(=O)=O 3 264 247
26 N Sulfonamide CNS(C)(=O)=O 3 264 247
27 S Sulfonamide CNS(C)(=O)=O 3 264 247
28 O Sulfonamide CNS(C)(=O)=O 3 264 247
29 O Sulfonamide CNS(C)(=O)=O 3 264 247
30 C NA CNS(C)(=O)=O 3 264 247
31 O Alkylarylether, Imidolactone CO 4 264 247
32 C Alkylarylether, Imidolactone CO 4 264 247
0 C Primary_carbon C 1 284 248
0 C Primary_carbon, Secondary_carbon C 1 316 250
0 C Enolether CO 1 851 253
1 O Enolether CO 1 851 253
14 O Enolether CO 2 851 253
15 C Enolether CO 2 851 253
0 C Primary_carbon CC(C)O 1 268 257
1 C Primary_carbon, Alkylarylether CC(C)O 1 268 257
2 C Primary_carbon CC(C)O 1 268 257
3 O Alkylarylether CC(C)O 1 268 257
0 C Primary_carbon, Secondary_carbon CCCCO 1 263 258
1 C Primary_carbon, Secondary_carbon CCCCO 1 263 258
2 C Secondary_carbon CCCCO 1 263 258
3 C Secondary_carbon, Urethan CCCCO 1 263 258
4 O Urethan CCCCO 1 263 258
6 O Urethan O 2 263 258
0 C NA CNC 1 289 259
1 N Urea CNC 1 289 259
2 C NA CNC 1 289 259
12 C Alkylfluoride, Trifluoromethyl FC(F)F 2 289 259
13 F Alkylfluoride, Trifluoromethyl FC(F)F 2 289 259
14 F Alkylfluoride, Trifluoromethyl FC(F)F 2 289 259
15 F Alkylfluoride, Trifluoromethyl FC(F)F 2 289 259
2 N Amidine, Conjugated_double_bond, Conjugated_tripple_bond N#CN 1 320 261
3 C Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N#CN 1 320 261
4 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N#CN 1 320 261
6 C NA C 2 320 261
12 Cl Imidoylhalide_cyclic, Arylchloride Cl 3 320 261
7 S NA S 1 285 265
7 O Conjugated_double_bond O 1 319 266
18 O Halogen_acetal_like, Acetal_like OC(F)(F)F 2 319 266
19 C Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 2 319 266
20 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 2 319 266
21 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 2 319 266
22 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 2 319 266
23 Cl Arylchloride Cl 3 319 266
10 O Alkylarylether CO 1 1004 268
11 C Alkylarylether CO 1 1004 268
12 O Phenol O 2 1004 268
4 C Secondary_carbon, Tertiary_carbon C1CC1 1 283 269
5 C Secondary_carbon, Tertiary_carbon C1CC1 1 283 269
6 C Secondary_carbon, Tertiary_carbon C1CC1 1 283 269
0 C Primary_carbon CC(C)N 1 393 273
1 C Primary_carbon CC(C)N 1 393 273
2 C Primary_carbon CC(C)N 1 393 273
3 N Secondary_aliph_amine, 1,2-Aminoalcohol CC(C)N 1 393 273
14 C Secondary_carbon CC(N)=O 2 393 273
15 C Secondary_carbon, Primary_amide CC(N)=O 2 393 273
16 O Primary_amide CC(N)=O 2 393 273
17 N Primary_amide CC(N)=O 2 393 273
0 C Secondary_amide CNC(=O)CS 1 285 274
1 N Secondary_amide CNC(=O)CS 1 285 274
2 C Secondary_amide CNC(=O)CS 1 285 274
3 O Secondary_amide CNC(=O)CS 1 285 274
4 C NA CNC(=O)CS 1 285 274
5 S NA CNC(=O)CS 1 285 274
7 S NA S 2 285 274
0 C Primary_carbon, Secondary_carbon C 1 316 275
3 C Primary_carbon C 2 316 275
14 O Alkylarylether CO 3 316 275
15 C Alkylarylether CO 3 316 275
0 C Primary_carbon, Tertiary_carbon C 1 311 276
2 C Primary_carbon, Tertiary_carbon C 2 311 276
3 C NA CCCl 1 482 277
4 C Alkylchloride CCCl 1 482 277
5 Cl Alkylchloride CCCl 1 482 277
13 Br Arylbromide Br 2 482 277
11 C Acetal, Acetal_like C1COCO1 1 302 280
12 O Acetal, Acetal_like, Heterocyclic C1COCO1 1 302 280
13 C Acetal C1COCO1 1 302 280
14 C Acetal C1COCO1 1 302 280
15 O Acetal, Acetal_like, Heterocyclic C1COCO1 1 302 280
0 C NA C 1 302 284
11 C Acetal, Acetal_like C1COCO1 2 302 284
12 O Acetal, Acetal_like, Heterocyclic C1COCO1 2 302 284
13 C Acetal C1COCO1 2 302 284
14 C Acetal C1COCO1 2 302 284
15 O Acetal, Acetal_like, Heterocyclic C1COCO1 2 302 284
0 C Primary_carbon CCC(=O)OC 1 294 285
1 C Primary_carbon, Conjugated_double_bond CCC(=O)OC 1 294 285
8 O NA CO 2 294 285
9 C NA CO 2 294 285
10 C Carboxylic_ester, Conjugated_double_bond CCC(=O)OC 1 294 285
11 O Carboxylic_ester, Conjugated_double_bond CCC(=O)OC 1 294 285
12 O Carboxylic_ester CCC(=O)OC 1 294 285
13 C Carboxylic_ester CCC(=O)OC 1 294 285
0 C Primary_carbon C 1 372 286
12 N Sulfonamide N 2 372 286
11 Br Arylbromide Br 1 295 289
12 O NA CO 2 295 289
13 C NA CO 2 295 289
0 C NA CCN(C)C 1 530 291
1 N Tertiary_aliph_amine CCN(C)C 1 530 291
2 C NA CCN(C)C 1 530 291
3 C NA CCN(C)C 1 530 291
4 C Dialkylether CCN(C)C 1 530 291
0 C Primary_carbon C 1 335 292
4 C Primary_carbon C 2 335 292
24 C Primary_carbon C 3 335 292
25 O Alkylarylether CO 4 335 292
26 C Alkylarylether CO 4 335 292
0 C Primary_carbon C 1 298 295
7 Cl Arylchloride Cl 2 298 295
13 C NA C 3 298 295
0 C Primary_carbon C 1 515 296
8 C Aromatic c1ccncc1 2 515 296
9 C Aromatic c1ccncc1 2 515 296
10 C Aromatic c1ccncc1 2 515 296
11 C Aromatic c1ccncc1 2 515 296
12 C Aromatic c1ccncc1 2 515 296
13 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 2 515 296
16 C NA CN(C)C 3 515 296
17 N Tertiary_aliph_amine CN(C)C 3 515 296
18 C NA CN(C)C 3 515 296
19 C NA CN(C)C 3 515 296
0 C Primary_carbon, Secondary_carbon CCCCN 1 411 299
1 C Primary_carbon, Secondary_carbon CCCCN 1 411 299
2 C Secondary_carbon CCCCN 1 411 299
3 C Secondary_carbon CCCCN 1 411 299
4 N Secondary_mixed_amine CCCCN 1 411 299
18 S Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 411 299
19 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 411 299
20 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 411 299
21 N Sulfonamide N[SH](=O)=O 2 411 299
22 C Carboxylic_acid, Conjugated_double_bond O=CO 3 411 299
23 O Carboxylic_acid, Conjugated_double_bond O=CO 3 411 299
24 O Carboxylic_acid O=CO 3 411 299
2 C Secondary_carbon, Tertiary_carbon C 1 350 300
6 C Secondary_carbon, Tertiary_carbon C 2 350 300
2 C NA C 1 303 301
4 O Urea O 2 303 301
6 C Aromatic c1ccccc1 3 303 301
7 C Aromatic c1ccccc1 3 303 301
8 C Aromatic c1ccccc1 3 303 301
9 C Aromatic c1ccccc1 3 303 301
10 C Aromatic c1ccccc1 3 303 301
11 C Aromatic c1ccccc1 3 303 301
0 C Primary_carbon C 1 307 302
6 C Primary_carbon C 2 307 302
8 S Alkylarylthioether CS 3 307 302
9 C Alkylarylthioether CS 3 307 302
12 Cl Arylchloride Cl 1 326 303
13 Cl Arylchloride Cl 2 326 303
0 C Primary_carbon CCC(C)(C)C 1 722 304
1 C Primary_carbon, Quaternary_carbon CCC(C)(C)C 1 722 304
2 C Primary_carbon, Quaternary_carbon CCC(C)(C)C 1 722 304
3 C Primary_carbon, Quaternary_carbon CCC(C)(C)C 1 722 304
4 C Primary_carbon, Quaternary_carbon CCC(C)(C)C 1 722 304
5 C Primary_carbon, Quaternary_carbon CCC(C)(C)C 1 722 304
8 N Guanidine, Conjugated_double_bond, Conjugated_tripple_bond N#CN 2 722 304
9 C Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N#CN 2 722 304
10 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N#CN 2 722 304
11 O Urethan CNC(=O)O 1 309 305
12 C Urethan CNC(=O)O 1 309 305
13 O Urethan CNC(=O)O 1 309 305
14 N Urethan CNC(=O)O 1 309 305
15 C NA CNC(=O)O 1 309 305
0 C Primary_carbon, Tertiary_carbon C 1 311 307
2 C Primary_carbon, Tertiary_carbon C 2 311 307
3 C Primary_carbon C 1 316 308
14 O Alkylarylether CO 2 316 308
15 C Alkylarylether CO 2 316 308
0 C Primary_carbon, Tertiary_carbon C 1 311 309
2 C Primary_carbon, Tertiary_carbon C 2 311 309
2 N Amidine, Conjugated_double_bond, Conjugated_tripple_bond N#CN 1 320 310
3 C Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N#CN 1 320 310
4 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N#CN 1 320 310
0 C Secondary_carbon CCC 1 815 311
1 C Secondary_carbon, Tertiary_carbon CCC 1 815 311
4 C Secondary_carbon, Tertiary_carbon C 2 815 311
7 C Secondary_carbon, Tertiary_carbon CCC 1 815 311
12 S NA S 3 815 311
13 S NA S 4 815 311
0 C Aromatic ccc 1 378 314
1 C Aromatic ccc 1 378 314
9 C Aromatic, Conjugated_double_bond ccc 1 378 314
11 O Imide_acidic, Conjugated_double_bond O 2 378 314
14 O Imide_acidic, Conjugated_double_bond O 3 378 314
15 N Primary_arom_amine N 4 378 314
2 C Primary_carbon, Tertiary_carbon C 1 947 315
2 C NA C 1 386 316
11 C NA C 2 386 316
12 N NA CNC 3 386 316
13 C NA CNC 3 386 316
14 C NA CNC 3 386 316
0 C Primary_carbon C 1 372 317
9 S Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 372 317
10 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 372 317
11 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 372 317
12 N Sulfonamide N[SH](=O)=O 2 372 317
0 C NA C 1 326 318
2 C NA C 2 326 318
12 Cl Arylchloride Cl 3 326 318
13 Cl Arylchloride Cl 4 326 318
8 S NA CS 1 334 322
9 C NA CS 1 334 322
8 C Aromatic c1cscn1 1 343 323
9 C Aromatic c1cscn1 1 343 323
10 S Hetero_S, Heteroaromatic, Aromatic, Heterocyclic c1cscn1 1 343 323
11 C Aromatic c1cscn1 1 343 323
12 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1cscn1 1 343 323
0 C Primary_carbon, Secondary_carbon C 1 794 325
18 C NA CN(C)C 2 794 325
19 N Tertiary_aliph_amine CN(C)C 2 794 325
20 C NA CN(C)C 2 794 325
21 C NA CN(C)C 2 794 325
22 C Aromatic, Conjugated_double_bond c1ccccc1 3 794 325
23 C Aromatic, Conjugated_double_bond c1ccccc1 3 794 325
24 C Aromatic c1ccccc1 3 794 325
25 C Aromatic c1ccccc1 3 794 325
26 C Aromatic c1ccccc1 3 794 325
27 C Aromatic, Conjugated_double_bond c1ccccc1 3 794 325
8 N Guanidine N 1 510 326
11 N Guanidine N 2 510 326
12 N Guanidine N 3 510 326
2 O Ketone, Conjugated_double_bond O 1 969 329
11 O Alkylarylether CO 2 969 329
12 C Alkylarylether CO 2 969 329
13 O Phenol O 3 969 329
9 O Phenol O 1 348 330
11 O Carboxylic_acid, Alpha_aminoacid O 2 348 330
12 O Carboxylic_acid, Alpha_aminoacid O 3 348 330
13 N Primary_aliph_amine, Alpha_aminoacid N 4 348 330
0 C Primary_carbon C 1 351 332
3 C Primary_carbon CC 2 351 332
4 C Primary_carbon CC 2 351 332
9 O Secondary_amide, Conjugated_double_bond O 3 351 332
16 N Secondary_amide CC(N)=O 4 351 332
17 C Primary_carbon, Secondary_amide CC(N)=O 4 351 332
18 O Secondary_amide CC(N)=O 4 351 332
19 C Primary_carbon CC(N)=O 4 351 332
6 O Halogen_acetal_like, Acetal_like OC(F)(F)F 1 737 333
7 C Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 1 737 333
8 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 1 737 333
9 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 1 737 333
10 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl OC(F)(F)F 1 737 333
8 O Tertiary_amide, Conjugated_double_bond O 1 336 334
9 N Tertiary_amide CNC 2 336 334
10 C Tertiary_amide CNC 2 336 334
11 C Tertiary_amide CNC 2 336 334
0 C Primary_carbon, Secondary_carbon CC 1 342 335
1 C Primary_carbon, Secondary_carbon CC 1 342 335
0 C Primary_carbon, Quaternary_carbon C 1 347 336
2 C Primary_carbon, Quaternary_carbon C 2 347 336
3 C Primary_carbon, Quaternary_carbon C 3 347 336
11 C Dialkylthioether CSC 4 347 336
12 S Dialkylthioether CSC 4 347 336
13 C Dialkylthioether CSC 4 347 336
0 C Aromatic c1ccccc1 1 410 338
1 C Aromatic c1ccccc1 1 410 338
2 C Aromatic, Conjugated_double_bond c1ccccc1 1 410 338
3 C Aromatic, Conjugated_double_bond c1ccccc1 1 410 338
4 C Aromatic, Conjugated_double_bond c1ccccc1 1 410 338
5 C Aromatic c1ccccc1 1 410 338
0 C Secondary_carbon C1CCCC1 1 463 343
1 C Secondary_carbon C1CCCC1 1 463 343
2 C Secondary_carbon C1CCCC1 1 463 343
3 C Secondary_carbon C1CCCC1 1 463 343
4 C Secondary_carbon C1CCCC1 1 463 343
9 C Primary_arom_amine, Imidolactam, Aromatic ncncN 2 463 343
10 N Primary_arom_amine ncncN 2 463 343
11 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ncncN 2 463 343
12 C Aromatic ncncN 2 463 343
13 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ncncN 2 463 343
2 O Carbothioic_S_ester O 1 376 347
5 C NA C[N+](C)(C)C 2 376 347
6 N Quaternary_aliph_ammonium, Ammonium, Kation C[N+](C)(C)C 2 376 347
7 C NA C[N+](C)(C)C 2 376 347
8 C NA C[N+](C)(C)C 2 376 347
9 C NA C[N+](C)(C)C 2 376 347
0 C Primary_carbon C 1 597 349
6 C Amidine, Conjugated_double_bond N=CN 1 380 350
7 N Amidine, Conjugated_double_bond N=CN 1 380 350
8 N Amidine N=CN 1 380 350
0 C Aromatic Cc1ccco1 1 585 353
1 C Aromatic Cc1ccco1 1 585 353
2 C Aromatic Cc1ccco1 1 585 353
3 C NA Cc1ccco1 1 585 353
14 O NA NS(=O)O 2 585 353
15 S NA NS(=O)O 2 585 353
16 O NA NS(=O)O 2 585 353
17 N NA NS(=O)O 2 585 353
18 Cl Arylchloride Cl 3 585 353
19 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic Cc1ccco1 1 585 353
20 C Aromatic Cc1ccco1 1 585 353
19 C Secondary_carbon CCN 1 383 355
20 C Secondary_carbon CCN 1 383 355
21 N Primary_aliph_amine CCN 1 383 355
0 C NA C 1 532 356
7 N Primary_arom_amine N 1 522 357
0 C Primary_carbon C 1 840 358
4 C Primary_carbon C 2 840 358
5 C Primary_carbon C 3 840 358
0 C Aromatic c1ccccc1 1 410 361
1 C Aromatic c1ccccc1 1 410 361
2 C Aromatic, Conjugated_double_bond c1ccccc1 1 410 361
3 C Aromatic, Conjugated_double_bond c1ccccc1 1 410 361
4 C Aromatic, Conjugated_double_bond c1ccccc1 1 410 361
5 C Aromatic c1ccccc1 1 410 361
8 N Primary_amide N 2 410 361
0 C Primary_carbon, CH-acidic CC(=O)S 1 376 363
1 C Primary_carbon, Carbothioic_S_ester CC(=O)S 1 376 363
2 O Carbothioic_S_ester CC(=O)S 1 376 363
3 S Carbothioic_S_ester CC(=O)S 1 376 363
14 O Lactam, Oxoarene, Conjugated_double_bond O 1 701 370
2 C Primary_alcohol CO 1 588 371
3 O Primary_alcohol CO 1 588 371
0 C Primary_carbon C 1 653 377
12 O Phenol O 2 653 377
0 C Alkylarylether CO 1 963 378
1 O Alkylarylether CO 1 963 378
12 C Aromatic cco 2 963 378
13 C Aromatic cco 2 963 378
14 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic cco 2 963 378
18 O Secondary_alcohol O 1 437 379
19 O Phenol, 1,2-Diphenol O 2 437 379
7 O Primary_amide, Conjugated_double_bond O 1 410 380
6 C Primary_amide, Conjugated_double_bond NC=O 1 519 381
7 O Primary_amide, Conjugated_double_bond NC=O 1 519 381
8 N Primary_amide NC=O 1 519 381
10 C Secondary_carbon CCN 2 519 381
11 C Secondary_carbon CCN 2 519 381
12 N Primary_aliph_amine CCN 2 519 381
0 C NA CN 1 652 383
1 N Secondary_aliph_amine CN 1 652 383
13 C Aromatic ccnc 2 652 383
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ccnc 2 652 383
15 C Aromatic ccnc 2 652 383
16 C Aromatic ccnc 2 652 383
20 O Phenol O 1 535 384
8 C Secondary_carbon, Carboxylic_acid O=CO 1 412 385
9 O Carboxylic_acid O=CO 1 412 385
10 O Carboxylic_acid O=CO 1 412 385
0 C Primary_alcohol CO 1 394 387
17 O Secondary_alcohol, 1,2-Diol O 2 394 387
18 O Primary_alcohol CO 1 394 387
0 C Alkyne C#CCO 1 400 388
1 C Alkyne C#CCO 1 400 388
2 C Carboxylic_ester C#CCO 1 400 388
3 O Carboxylic_ester C#CCO 1 400 388
5 O Carboxylic_ester, Conjugated_double_bond O 2 400 388
7 C Secondary_carbon, Alkene, Conjugated_double_bond CCCN(C)C 3 400 388
8 C Secondary_carbon CCCN(C)C 3 400 388
9 C Secondary_carbon CCCN(C)C 3 400 388
10 N Tertiary_aliph_amine, Heterocyclic CCCN(C)C 3 400 388
11 C NA CCCN(C)C 3 400 388
12 C NA CCCN(C)C 3 400 388
0 C Primary_carbon, Secondary_carbon CCC 1 442 390
1 C Primary_carbon, Secondary_carbon CCC 1 442 390
2 C Secondary_carbon CCC 1 442 390
16 Cl Arylchloride Cl 2 442 390
0 C Primary_carbon CC 1 807 391
1 C Primary_carbon, Tertiary_amide CC 1 807 391
11 O Tertiary_amide O 2 807 391
14 O Primary_alcohol O 3 807 391
15 C Tertiary_carbon, Aromatic c1ccccc1 4 807 391
16 C Aromatic c1ccccc1 4 807 391
17 C Aromatic c1ccccc1 4 807 391
18 C Aromatic c1ccccc1 4 807 391
19 C Aromatic c1ccccc1 4 807 391
20 C Aromatic c1ccccc1 4 807 391
0 C Primary_carbon, Secondary_carbon CCC 1 797 392
1 C Primary_carbon, Secondary_carbon CCC 1 797 392
2 C Secondary_carbon CCC 1 797 392
4 C Secondary_carbon CCC 2 797 392
5 C Primary_carbon, Secondary_carbon CCC 2 797 392
6 C Primary_carbon, Secondary_carbon CCC 2 797 392
16 O Alkylarylether CO 3 797 392
17 C Alkylarylether CO 3 797 392
18 O Alkylarylether CO 4 797 392
19 C Alkylarylether CO 4 797 392
16 O Dialkylether CO 1 903 393
17 C Dialkylether CO 1 903 393
13 Cl Arylchloride Cl 1 479 394
0 C Primary_carbon, Secondary_carbon CCC 1 703 395
1 C Primary_carbon, Secondary_carbon CCC 1 703 395
2 C Secondary_carbon CCC 1 703 395
15 O Phenol O 2 703 395
16 O Phenol O 1 437 397
18 O Secondary_alcohol O 2 437 397
19 O Phenol, 1,2-Diphenol O 3 437 397
20 O Phenol, 1,2-Diphenol O 4 437 397
7 O Primary_amide, Conjugated_double_bond O 1 410 398
8 N Primary_amide N 2 410 398
0 C Primary_carbon, Secondary_carbon CC 1 402 399
1 C Primary_carbon, Secondary_carbon CC 1 402 399
10 C Primary_carbon, Secondary_carbon CC 2 402 399
11 C Primary_carbon, Secondary_carbon CC 2 402 399
10 C Aromatic cccc 1 929 404
11 C Aromatic cccc 1 929 404
12 C Aromatic cccc 1 929 404
13 C Aromatic, Conjugated_double_bond cccc 1 929 404
16 O Oxoarene, Conjugated_double_bond O 2 929 404
14 C Aromatic cc[nH] 1 516 405
15 C Aromatic cc[nH] 1 516 405
16 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic cc[nH] 1 516 405
6 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 1 512 408
7 O Anion O=[NH+][O-] 1 512 408
8 O Conjugated_double_bond O=[NH+][O-] 1 512 408
9 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 2 512 408
10 O Anion O=[NH+][O-] 2 512 408
11 O Conjugated_double_bond O=[NH+][O-] 2 512 408
14 O Lactam, Oxoarene, Conjugated_double_bond O 3 512 408
16 O Lactam, Oxoarene, Conjugated_double_bond O 4 512 408
27 F Alkylfluoride F 1 435 409
7 N Amidine, Conjugated_double_bond N 1 429 410
0 C NA C[SH](=O)=O 1 669 411
1 S Sulfonamide C[SH](=O)=O 1 669 411
2 O Sulfonamide C[SH](=O)=O 1 669 411
3 O Sulfonamide C[SH](=O)=O 1 669 411
18 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 2 669 411
19 O Anion O=[NH+][O-] 2 669 411
20 O Conjugated_double_bond O=[NH+][O-] 2 669 411
11 N Primary_aliph_amine, Alpha_aminoacid N 1 472 412
0 C Alkyne C 1 546 415
0 C Primary_carbon, Tertiary_carbon C 1 435 418
25 O Tertiary_alcohol O 2 435 418
27 F Alkylfluoride F 3 435 418
0 C NA CNCCN 1 652 420
1 N Secondary_aliph_amine CNCCN 1 652 420
2 C NA CNCCN 1 652 420
3 C NA CNCCN 1 652 420
4 N Sulfonamide CNCCN 1 652 420
13 C Aromatic ccnc 2 652 420
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic ccnc 2 652 420
15 C Aromatic ccnc 2 652 420
16 C Aromatic ccnc 2 652 420
0 C Primary_carbon C 1 570 421
18 Cl Arylchloride Cl 2 570 421
19 Cl Arylchloride Cl 3 570 421
20 C Carboxylic_ester, Conjugated_double_bond COC=O 4 570 421
21 O Carboxylic_ester, Conjugated_double_bond COC=O 4 570 421
22 O Carboxylic_ester COC=O 4 570 421
23 C Carboxylic_ester COC=O 4 570 421
23 Cl Arylchloride Cl 1 511 424
0 C NA C 1 804 425
10 O Alkylarylether CO 2 804 425
11 C Alkylarylether CO 2 804 425
22 O Alkylarylether CO 3 804 425
23 C Alkylarylether CO 3 804 425
24 O Alkylarylether CO 4 804 425
25 C Alkylarylether CO 4 804 425
0 C Primary_carbon, Secondary_carbon CCC 1 629 426
1 C Primary_carbon, Secondary_carbon CCC 1 629 426
2 C Secondary_carbon CCC 1 629 426
7 C Primary_carbon, Secondary_carbon C 2 629 426
17 C Carboxylic_ester, Conjugated_double_bond CCCOC=O 3 629 426
18 O Carboxylic_ester, Conjugated_double_bond CCCOC=O 3 629 426
19 O Carboxylic_ester CCCOC=O 3 629 426
20 C Secondary_carbon, Carboxylic_ester CCCOC=O 3 629 426
21 C Primary_carbon, Secondary_carbon CCCOC=O 3 629 426
22 C Primary_carbon, Secondary_carbon CCCOC=O 3 629 426
23 C Carbothioic_S_ester, Conjugated_double_bond CCSC=O 4 629 426
24 O Carbothioic_S_ester, Conjugated_double_bond CCSC=O 4 629 426
25 S Carbothioic_S_ester CCSC=O 4 629 426
26 C Primary_carbon, Carbothioic_S_ester CCSC=O 4 629 426
27 C Primary_carbon CCSC=O 4 629 426
7 N Amidine, Conjugated_double_bond N 1 429 427
0 C Primary_carbon C 1 556 429
8 Cl Arylchloride Cl 2 556 429
9 Cl Arylchloride Cl 3 556 429
0 C Primary_carbon C 1 857 430
4 O Ketone, Conjugated_double_bond O 2 857 430
11 S Alkylarylthioether CS 3 857 430
12 C Alkylarylthioether CS 3 857 430
27 O Secondary_alcohol, 1,2-Diol O 1 784 435
9 O Oxoarene, Conjugated_double_bond O 1 705 437
23 O Ketone O 1 446 438
25 O Tertiary_alcohol O 2 446 438
0 C Primary_carbon, Secondary_carbon C 1 772 442
15 C Primary_carbon C 2 772 442
12 Cl Arylchloride Cl 1 458 443
15 O Tertiary_amide, Conjugated_double_bond O 1 880 445
24 O Secondary_alcohol O 1 594 446
19 Cl Chloroalkene Cl 1 455 447
0 C Primary_carbon, Secondary_carbon CCC=O 1 699 449
1 C Primary_carbon, Secondary_carbon, Ketone, CH-acidic CCC=O 1 699 449
2 C Secondary_carbon, Ketone, Conjugated_double_bond CCC=O 1 699 449
3 O Ketone, Conjugated_double_bond CCC=O 1 699 449
6 C Primary_carbon C 1 486 450
7 C Primary_carbon C 2 486 450
6 C Carboxylic_acid, Conjugated_double_bond O=CO 1 464 451
7 O Carboxylic_acid, Conjugated_double_bond O=CO 1 464 451
8 O Carboxylic_acid O=CO 1 464 451
9 Hg Organometallic_compounds, Halogen_on_hetero Cl[Hg] 2 464 451
10 Cl Halogen_on_hetero Cl[Hg] 2 464 451
6 Cl Arylchloride Cl 1 460 452
7 N Guanidine NC1=NCCN1 2 460 452
8 C Guanidine NC1=NCCN1 2 460 452
9 N Guanidine, Heterocyclic NC1=NCCN1 2 460 452
10 C NA NC1=NCCN1 2 460 452
11 C NA NC1=NCCN1 2 460 452
12 N Guanidine, Heterocyclic NC1=NCCN1 2 460 452
8 N Guanidine N 1 510 453
10 C Guanidine N=CN 2 510 453
11 N Guanidine N=CN 2 510 453
12 N Guanidine N=CN 2 510 453
13 Cl Arylchloride Cl 3 510 453
0 C Primary_carbon CC 1 550 454
1 C Primary_carbon, Secondary_amide CC 1 550 454
0 C Primary_carbon, CH-acidic COC(C)=O 1 467 455
1 C Primary_carbon, Carboxylic_ester COC(C)=O 1 467 455
2 O Carboxylic_ester COC(C)=O 1 467 455
3 O Carboxylic_ester COC(C)=O 1 467 455
4 C Carboxylic_ester COC(C)=O 1 467 455
21 N Oximether, Conjugated_double_bond CON 2 467 455
22 O Oximether CON 2 467 455
23 C Oximether CON 2 467 455
24 C Aromatic, Conjugated_double_bond Nc1nccs1 3 467 455
25 C Aromatic, Conjugated_double_bond Nc1nccs1 3 467 455
26 S Isothiourea, Hetero_S, Heteroaromatic, Aromatic, Heterocyclic Nc1nccs1 3 467 455
27 C Primary_arom_amine, Isothiourea, Aromatic Nc1nccs1 3 467 455
28 N Primary_arom_amine, Isothiourea Nc1nccs1 3 467 455
29 N Isothiourea, Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond Nc1nccs1 3 467 455
0 C NA CNC 1 530 457
1 N Tertiary_aliph_amine CNC 1 530 457
2 C NA CNC 1 530 457
0 C Primary_carbon C 1 853 459
2 C Primary_carbon C 2 853 459
19 C Quaternary_carbon, Primary_amide NC=O 3 853 459
20 O Primary_amide NC=O 3 853 459
21 N Primary_amide NC=O 3 853 459
23 C Primary_carbon C 4 853 459
24 C Primary_carbon C 5 853 459
13 I Aryliodide I 1 617 460
24 O Secondary_alcohol O 1 594 462
0 C NA C 1 532 463
7 O Lactam, Oxoarene, Conjugated_double_bond O 2 532 463
9 C NA C 3 532 463
11 O Urea, Oxoarene, Conjugated_double_bond O 4 532 463
0 C Primary_carbon C 1 556 464
8 Cl Arylchloride Cl 2 556 464
9 Cl Arylchloride Cl 3 556 464
10 N Primary_aliph_amine N 4 556 464
17 C Secondary_carbon, Alkene C1=CCC=CC1 1 475 467
18 C Secondary_carbon, Alkene C1=CCC=CC1 1 475 467
19 C Secondary_carbon C1=CCC=CC1 1 475 467
20 C Secondary_carbon, Alkene C1=CCC=CC1 1 475 467
21 C Secondary_carbon, Alkene C1=CCC=CC1 1 475 467
22 C Secondary_carbon C1=CCC=CC1 1 475 467
23 N Primary_aliph_amine, Peptide_N_term N 2 475 467
0 C Primary_carbon, Secondary_carbon CC 1 583 471
1 C Primary_carbon, Secondary_carbon, Quaternary_carbon CC 1 583 471
3 C Primary_carbon, Quaternary_carbon C 2 583 471
9 O Imide_acidic O 3 583 471
0 C Carboxylic_ester C 1 491 472
0 C Alkylarylether CO 1 654 473
1 O Alkylarylether CO 1 654 473
17 C Tertiary_amide, Imidolactam, Aromatic c1ccncc1 2 654 473
18 C Imidolactam, Aromatic c1ccncc1 2 654 473
19 C Aromatic c1ccncc1 2 654 473
20 C Aromatic c1ccncc1 2 654 473
21 C Aromatic c1ccncc1 2 654 473
22 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 2 654 473
31 F Arylfluoride F 3 654 473
0 C Primary_carbon CCN 1 550 479
1 C Primary_carbon, Secondary_amide CCN 1 550 479
2 N Secondary_amide CCN 1 550 479
4 O Secondary_amide O 2 550 479
0 C Primary_carbon, Secondary_carbon CCCC 1 579 481
1 C Primary_carbon, Secondary_carbon CCCC 1 579 481
2 C Secondary_carbon CCCC 1 579 481
3 C Secondary_carbon CCCC 1 579 481
6 O Tertiary_amide, Conjugated_double_bond O 1 544 482
13 O Alkylarylether CO 2 544 482
14 C Alkylarylether CO 2 544 482
15 O Phenol O 3 544 482
6 C Aromatic c1ccncc1 1 551 485
7 C Aromatic c1ccncc1 1 551 485
8 C Aromatic c1ccncc1 1 551 485
9 C Aromatic c1ccncc1 1 551 485
10 C Aromatic c1ccncc1 1 551 485
11 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 1 551 485
0 C Primary_carbon C 1 630 486
6 C Primary_carbon C 2 630 486
11 C Primary_carbon C 3 630 486
12 N Primary_aliph_amine N 4 630 486
11 Cl Arylchloride Cl 1 504 488
10 N Hydrazine NN 1 593 489
11 N Hydrazine NN 1 593 489
12 O Phenol, 1,2-Diphenol O 1 540 491
13 O Phenol, 1,2-Diphenol O 2 540 491
22 F Arylfluoride F 1 580 494
29 F Arylfluoride F 2 580 494
0 C Primary_carbon C 1 556 496
8 Cl Arylchloride Cl 2 556 496
9 Cl Arylchloride Cl 3 556 496
10 N Primary_aliph_amine N 4 556 496
9 C NA CCS 1 879 501
10 C NA CCS 1 879 501
11 S Isothiourea, Heterocyclic CCS 1 879 501
0 C Primary_carbon CCN 1 550 502
1 C Primary_carbon, Secondary_amide CCN 1 550 502
2 N Secondary_amide CCN 1 550 502
4 O Secondary_amide O 2 550 502
0 C Primary_carbon CCN 1 550 504
1 C Primary_carbon, Secondary_amide CCN 1 550 504
2 N Secondary_amide CCN 1 550 504
4 O Secondary_amide O 2 550 504
0 C Alkene C=C 1 657 506
1 C Alkene C=C 1 657 506
13 O Alkylarylether, Heterocyclic O 2 657 506
16 O Ketone O 3 657 506
22 O Tertiary_alcohol, 1,2-Aminoalcohol O 4 657 506
5 C Primary_carbon C 1 943 507
12 C Primary_carbon, Quaternary_carbon C 2 943 507
13 C Primary_carbon, Quaternary_carbon C 3 943 507
0 C Alkene C 1 943 509
10 C Secondary_carbon, Tertiary_carbon, Quaternary_carbon CC(C)C 2 943 509
11 C Primary_carbon, Secondary_carbon, Tertiary_carbon, Quaternary_carbon CC(C)C 2 943 509
12 C Primary_carbon, Quaternary_carbon CC(C)C 2 943 509
13 C Primary_carbon, Quaternary_carbon CC(C)C 2 943 509
14 O Dialkylether, Heterocyclic, Epoxide O 3 943 509
12 Cl Arylchloride Cl 1 861 512
13 Cl Arylchloride Cl 2 861 512
2 C Primary_carbon C 1 517 515
3 C Secondary_carbon CCC=[NH+][O-] 2 517 515
4 C Secondary_carbon, CH-acidic CCC=[NH+][O-] 2 517 515
5 C Secondary_carbon CCC=[NH+][O-] 2 517 515
6 N N-Oxide, Heterocyclic, Kation CCC=[NH+][O-] 2 517 515
7 O Anion CCC=[NH+][O-] 2 517 515
0 C Secondary_carbon CCCCC 1 589 517
1 C Secondary_carbon CCCCC 1 589 517
2 C Secondary_carbon, Quaternary_carbon CCCCC 1 589 517
4 C Secondary_carbon, Quaternary_carbon CCCCC 1 589 517
5 C Secondary_carbon CCCCC 1 589 517
7 C Secondary_carbon, Carboxylic_acid O=CO 2 589 517
8 O Carboxylic_acid O=CO 2 589 517
9 O Carboxylic_acid O=CO 2 589 517
10 C Quaternary_carbon CN 3 589 517
11 N Primary_aliph_amine CN 3 589 517
0 C Primary_carbon, Secondary_carbon CCC=O 1 699 518
1 C Primary_carbon, Secondary_carbon, Ketone, CH-acidic CCC=O 1 699 518
2 C Secondary_carbon, Ketone, Conjugated_double_bond CCC=O 1 699 518
3 O Ketone, Conjugated_double_bond CCC=O 1 699 518
14 N Tertiary_aliph_amine CNC 2 699 518
15 C NA CNC 2 699 518
16 C NA CNC 2 699 518
0 C Primary_carbon CC=O 1 600 519
1 C Primary_carbon, Secondary_amide CC=O 1 600 519
2 O Secondary_amide CC=O 1 600 519
15 I Aryliodide I 2 600 519
16 O Alkylarylether CO 3 600 519
17 C Alkylarylether CO 3 600 519
0 C Primary_carbon C 1 630 520
6 C Primary_carbon C 2 630 520
10 C Primary_carbon CCN 3 630 520
11 C Primary_carbon CCN 3 630 520
12 N Primary_aliph_amine CCN 3 630 520
0 C Primary_carbon, Tertiary_carbon C 1 773 521
5 C NA C 2 773 521
9 O Lactam, Oxoarene, Conjugated_double_bond O 1 586 522
13 F Arylfluoride F 2 586 522
15 O Secondary_alcohol, 1,2-Diol O 3 586 522
16 O Secondary_alcohol, 1,2-Diol O 4 586 522
11 C Aromatic ccc(O)cO 1 535 523
12 C Aromatic ccc(O)cO 1 535 523
13 C Phenol, 1,2-Diphenol, Aromatic ccc(O)cO 1 535 523
14 C Phenol, 1,2-Diphenol, Aromatic ccc(O)cO 1 535 523
15 O Phenol, 1,2-Diphenol ccc(O)cO 1 535 523
16 O Phenol, 1,2-Diphenol ccc(O)cO 1 535 523
20 O Phenol O 2 535 523
19 C Primary_amide, Conjugated_double_bond NC=O 1 876 525
20 O Primary_amide, Conjugated_double_bond NC=O 1 876 525
21 N Primary_amide NC=O 1 876 525
23 O Secondary_alcohol, 1,2-Aminoalcohol O 2 876 525
14 C Aromatic cc[nH] 1 690 528
15 C Aromatic cc[nH] 1 690 528
16 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic cc[nH] 1 690 528
7 C Secondary_carbon, Alpha_aminoacid NCC(=O)O 1 540 530
8 C Carboxylic_acid, Alpha_aminoacid NCC(=O)O 1 540 530
9 O Carboxylic_acid, Alpha_aminoacid NCC(=O)O 1 540 530
10 O Carboxylic_acid, Alpha_aminoacid NCC(=O)O 1 540 530
11 N Primary_aliph_amine, Alpha_aminoacid NCC(=O)O 1 540 530
12 O Phenol, 1,2-Diphenol O 2 540 530
13 O Phenol, 1,2-Diphenol O 3 540 530
0 C Primary_carbon CC 1 868 531
1 C Primary_carbon CC 1 868 531
4 C Aromatic cc(Cl)c(c)Cl 2 868 531
5 C Arylchloride, Aromatic cc(Cl)c(c)Cl 2 868 531
6 C Arylchloride, Aromatic cc(Cl)c(c)Cl 2 868 531
7 C Aromatic cc(Cl)c(c)Cl 2 868 531
12 Cl Arylchloride cc(Cl)c(c)Cl 2 868 531
13 Cl Arylchloride cc(Cl)c(c)Cl 2 868 531
0 C Alkyne C#C 1 865 532
1 C Alkyne C#C 1 865 532
13 C NA C 2 865 532
0 C Primary_carbon C 1 587 533
8 C Aromatic c1ccoc1 2 587 533
9 C Aromatic c1ccoc1 2 587 533
10 C Aromatic c1ccoc1 2 587 533
11 C Aromatic c1ccoc1 2 587 533
12 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic c1ccoc1 2 587 533
5 O Ketone, Conjugated_double_bond O 1 594 534
16 O Ketone O 2 594 534
17 C Primary_alcohol, Ketone CO 3 594 534
18 O Primary_alcohol CO 3 594 534
24 O Secondary_alcohol O 4 594 534
17 C Alkylarylether C 1 862 535
0 C Alkylarylether C 1 742 537
8 O Alkylarylether OC1CCCC1 2 742 537
9 C Secondary_carbon, Alkylarylether OC1CCCC1 2 742 537
10 C Secondary_carbon OC1CCCC1 2 742 537
11 C Secondary_carbon OC1CCCC1 2 742 537
12 C Secondary_carbon OC1CCCC1 2 742 537
13 C Secondary_carbon OC1CCCC1 2 742 537
17 O Lactam O 3 742 537
12 I Aryliodide I 1 622 540
0 C Primary_carbon C 1 739 542
19 Cl Arylchloride Cl 2 739 542
20 O Phenol, 1,2-Diphenol O 3 739 542
0 C Primary_carbon C 1 556 544
8 Cl Arylchloride Cl 2 556 544
9 Cl Arylchloride Cl 3 556 544
0 C Primary_carbon, Secondary_carbon C 1 621 546
10 O Phenol, 1,2-Diphenol O 2 621 546
11 O Phenol, 1,2-Diphenol O 3 621 546
12 O Secondary_alcohol, 1,2-Aminoalcohol O 4 621 546
16 C Primary_carbon C 5 621 546
0 C Primary_carbon, Secondary_carbon CC 1 621 548
1 C Primary_carbon, Secondary_carbon CC 1 621 548
12 O Secondary_alcohol, 1,2-Aminoalcohol O 2 621 548
16 C Primary_carbon C 3 621 548
7 S Thionitrite, Nitroso O=NS 1 648 549
8 N Thionitrite, Nitroso O=NS 1 648 549
9 O Thionitrite, Nitroso O=NS 1 648 549
12 N Secondary_amide, Peptide_C_term NCC(=O)O 2 648 549
13 C Secondary_amide, Peptide_C_term NCC(=O)O 2 648 549
14 C Carboxylic_acid, Peptide_C_term NCC(=O)O 2 648 549
15 O Carboxylic_acid, Peptide_C_term NCC(=O)O 2 648 549
16 O Carboxylic_acid, Peptide_C_term NCC(=O)O 2 648 549
18 C Carboxylic_acid, Alpha_aminoacid O=CO 3 648 549
19 O Carboxylic_acid, Alpha_aminoacid O=CO 3 648 549
20 O Carboxylic_acid, Alpha_aminoacid O=CO 3 648 549
21 N Primary_aliph_amine, Alpha_aminoacid N 4 648 549
0 C Primary_carbon, Secondary_carbon CCCC 1 579 551
1 C Primary_carbon, Secondary_carbon CCCC 1 579 551
2 C Secondary_carbon CCCC 1 579 551
3 C Secondary_carbon CCCC 1 579 551
8 C Carboxylic_acid, Conjugated_double_bond O=CO 2 579 551
9 O Carboxylic_acid, Conjugated_double_bond O=CO 2 579 551
10 O Carboxylic_acid O=CO 2 579 551
7 O Ketone, Conjugated_double_bond O 1 961 553
16 O Phenol, 1,2-Diphenol O 2 961 553
17 O Phenol, 1,2-Diphenol O 3 961 553
18 O Phenol O 4 961 553
0 C NA CCCN(C)C 1 887 555
1 N Tertiary_aliph_amine CCCN(C)C 1 887 555
2 C NA CCCN(C)C 1 887 555
3 C Secondary_carbon CCCN(C)C 1 887 555
4 C Secondary_carbon CCCN(C)C 1 887 555
5 C Secondary_carbon CCCN(C)C 1 887 555
0 C NA C 1 1008 556
3 O Secondary_amide O 1 648 558
6 C NA CSN=O 2 648 558
7 S Thionitrite, Nitroso CSN=O 2 648 558
8 N Thionitrite, Nitroso CSN=O 2 648 558
9 O Thionitrite, Nitroso CSN=O 2 648 558
11 O Secondary_amide O 3 648 558
14 C Carboxylic_acid, Peptide_C_term O=CO 4 648 558
15 O Carboxylic_acid, Peptide_C_term O=CO 4 648 558
16 O Carboxylic_acid, Peptide_C_term O=CO 4 648 558
18 C Carboxylic_acid, Alpha_aminoacid O=CO 5 648 558
19 O Carboxylic_acid, Alpha_aminoacid O=CO 5 648 558
20 O Carboxylic_acid, Alpha_aminoacid O=CO 5 648 558
10 C Secondary_carbon CN 1 635 559
11 N Primary_aliph_amine CN 1 635 559
8 O Carboxylic_acid O 1 589 564
9 O Carboxylic_acid O 2 589 564
10 C Quaternary_carbon CN 3 589 564
11 N Primary_aliph_amine CN 3 589 564
2 C Primary_carbon, Tertiary_carbon C 1 605 568
8 O Lactam, Oxoarene, Conjugated_double_bond O 2 605 568
10 C NA C 3 605 568
12 O Urea, Oxoarene, Conjugated_double_bond O 4 605 568
8 C Secondary_carbon CCC 1 886 569
9 C Secondary_carbon CCC 1 886 569
10 C Secondary_carbon CCC 1 886 569
23 O Alkylarylether CO 2 886 569
24 C Alkylarylether CO 2 886 569
10 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 1 650 570
11 O Anion O=[NH+][O-] 1 650 570
12 O Conjugated_double_bond O=[NH+][O-] 1 650 570
0 C Alkylarylether C 1 714 572
19 O Alkylarylether CO 2 714 572
20 C Alkylarylether CO 2 714 572
21 O Alkylarylether CO 3 714 572
22 C Alkylarylether CO 3 714 572
3 C Aromatic c[nH]n 1 661 573
4 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic c[nH]n 1 661 573
5 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c[nH]n 1 661 573
10 O Anion [OH-] 2 661 573
11 O Conjugated_double_bond O 3 661 573
0 C Primary_carbon, Quaternary_carbon C 1 952 574
0 C Secondary_amide CN 1 584 578
1 N Secondary_amide CN 1 584 578
0 C Aromatic cccc 1 701 579
1 C Aromatic cccc 1 701 579
2 C Aromatic, Conjugated_double_bond cccc 1 701 579
5 C Aromatic cccc 1 701 579
7 C Aromatic cccc 2 701 579
8 C Aromatic cccc 2 701 579
9 C Aromatic cccc 2 701 579
10 C Aromatic cccc 2 701 579
14 O Lactam, Oxoarene, Conjugated_double_bond O 3 701 579
0 C Alkylarylether CO 1 635 582
1 O Alkylarylether CO 1 635 582
10 C Secondary_carbon CN 2 635 582
11 N Primary_aliph_amine CN 2 635 582
0 C Alkene C 1 614 583
8 C Secondary_carbon, Tertiary_carbon CC(=O)O 2 614 583
9 C Secondary_carbon, Carboxylic_acid CC(=O)O 2 614 583
10 O Carboxylic_acid CC(=O)O 2 614 583
11 O Carboxylic_acid CC(=O)O 2 614 583
12 C Carboxylic_acid, Alpha_aminoacid O=CO 3 614 583
13 O Carboxylic_acid, Alpha_aminoacid O=CO 3 614 583
14 O Carboxylic_acid, Alpha_aminoacid O=CO 3 614 583
0 C Primary_carbon C 1 597 584
0 C Primary_carbon, Secondary_carbon CC 1 603 585
1 C Primary_carbon, Secondary_carbon CC 1 603 585
4 C Secondary_carbon CCC 2 603 585
5 C Primary_carbon, Secondary_carbon CCC 2 603 585
6 C Primary_carbon, Secondary_carbon CCC 2 603 585
11 C Aromatic ccc(c)O 3 603 585
12 C Aromatic ccc(c)O 3 603 585
13 C Phenol, Aromatic ccc(c)O 3 603 585
14 C Aromatic ccc(c)O 3 603 585
17 O Phenol ccc(c)O 3 603 585
0 C Primary_carbon, Tertiary_carbon CCC 1 605 587
1 C Primary_carbon, Tertiary_carbon CCC 1 605 587
2 C Primary_carbon, Tertiary_carbon CCC 1 605 587
0 C Primary_carbon C 1 868 588
4 C Aromatic cc(Cl)c(c)Cl 2 868 588
5 C Arylchloride, Aromatic cc(Cl)c(c)Cl 2 868 588
6 C Arylchloride, Aromatic cc(Cl)c(c)Cl 2 868 588
7 C Aromatic cc(Cl)c(c)Cl 2 868 588
11 O Urea, Oxoarene, Conjugated_double_bond O 3 868 588
12 Cl Arylchloride cc(Cl)c(c)Cl 2 868 588
13 Cl Arylchloride cc(Cl)c(c)Cl 2 868 588
2 O Ketone, Conjugated_double_bond O 1 969 589
9 O Alkylarylether CO 2 969 589
10 C Alkylarylether CO 2 969 589
11 O Alkylarylether CO 3 969 589
12 C Alkylarylether CO 3 969 589
13 O Phenol O 4 969 589
6 C Alkylfluoride, Trifluoromethyl FC(F)F 1 816 590
7 F Alkylfluoride, Trifluoromethyl FC(F)F 1 816 590
8 F Alkylfluoride, Trifluoromethyl FC(F)F 1 816 590
9 F Alkylfluoride, Trifluoromethyl FC(F)F 1 816 590
9 O Dialkylether, Heterocyclic, Epoxide O 1 744 592
14 C Tertiary_carbon, Primary_alcohol CO 2 744 592
15 O Primary_alcohol CO 2 744 592
6 N Acetal_like, NOS_methylen_ester_and_similar, Hetero_methylen_ester_and_similar, Heterocyclic NCN[SH](=O)=O 1 602 593
7 C Acetal_like, NOS_methylen_ester_and_similar, Hetero_methylen_ester_and_similar NCN[SH](=O)=O 1 602 593
8 N Acetal_like, NOS_methylen_ester_and_similar, Hetero_methylen_ester_and_similar, Sulfonamide, Heterocyclic NCN[SH](=O)=O 1 602 593
9 S Sulfonamide, Heterocyclic, Conjugated_double_bond NCN[SH](=O)=O 1 602 593
10 O Sulfonamide, Conjugated_double_bond NCN[SH](=O)=O 1 602 593
11 O Sulfonamide, Conjugated_double_bond NCN[SH](=O)=O 1 602 593
12 S Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 602 593
13 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 602 593
14 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 2 602 593
15 N Sulfonamide N[SH](=O)=O 2 602 593
16 Cl Arylchloride Cl 3 602 593
9 N Nitro, Conjugated_double_bond, Kation O=[NH+][O-] 1 661 595
10 O Anion O=[NH+][O-] 1 661 595
11 O Conjugated_double_bond O=[NH+][O-] 1 661 595
0 C Alkene C=CC 1 614 597
1 C Primary_carbon, Tertiary_carbon, Alkene C=CC 1 614 597
2 C Primary_carbon C=CC 1 614 597
8 C Secondary_carbon, Tertiary_carbon CC(=O)O 2 614 597
9 C Secondary_carbon, Carboxylic_acid CC(=O)O 2 614 597
10 O Carboxylic_acid CC(=O)O 2 614 597
11 O Carboxylic_acid CC(=O)O 2 614 597
12 C Carboxylic_acid, Alpha_aminoacid O=CO 3 614 597
13 O Carboxylic_acid, Alpha_aminoacid O=CO 3 614 597
14 O Carboxylic_acid, Alpha_aminoacid O=CO 3 614 597
25 O Alkylarylether CO 1 662 598
26 C Alkylarylether CO 1 662 598
17 O Phenol O 1 601 600
6 I Aryliodide I 1 607 602
7 C NA CN=C(N)N 2 607 602
8 N Guanidine CN=C(N)N 2 607 602
9 C Guanidine CN=C(N)N 2 607 602
10 N Guanidine CN=C(N)N 2 607 602
11 N Guanidine CN=C(N)N 2 607 602
17 F Arylfluoride F 1 818 603
18 O Phenol O 2 818 603
10 C Primary_carbon, Secondary_carbon CC 1 860 605
11 C Primary_carbon, Secondary_carbon CC 1 860 605
15 C NA C 2 860 605
0 C Primary_carbon, Secondary_carbon CC 1 629 606
1 C Primary_carbon, Secondary_carbon CC 1 629 606
6 C Primary_carbon, Secondary_carbon CC 2 629 606
7 C Primary_carbon, Secondary_carbon CC 2 629 606
10 C Aromatic c1ccccc1 3 629 606
11 C Aromatic c1ccccc1 3 629 606
12 C Aromatic c1ccccc1 3 629 606
13 C Aromatic c1ccccc1 3 629 606
14 C Aromatic c1ccccc1 3 629 606
15 C Aromatic c1ccccc1 3 629 606
17 C Carboxylic_ester, Conjugated_double_bond CCCOC=O 4 629 606
18 O Carboxylic_ester, Conjugated_double_bond CCCOC=O 4 629 606
19 O Carboxylic_ester CCCOC=O 4 629 606
20 C Secondary_carbon, Carboxylic_ester CCCOC=O 4 629 606
21 C Primary_carbon, Secondary_carbon CCCOC=O 4 629 606
22 C Primary_carbon, Secondary_carbon CCCOC=O 4 629 606
23 C Carbothioic_S_ester, Conjugated_double_bond CCSC=O 5 629 606
24 O Carbothioic_S_ester, Conjugated_double_bond CCSC=O 5 629 606
25 S Carbothioic_S_ester CCSC=O 5 629 606
26 C Primary_carbon, Carbothioic_S_ester CCSC=O 5 629 606
27 C Primary_carbon CCSC=O 5 629 606
0 C Alkyne C#CC 1 716 607
1 C Alkyne C#CC 1 716 607
2 C NA C#CC 1 716 607
4 C NA C 2 716 607
0 C Primary_carbon CCN(C)CC 1 620 610
1 C Primary_carbon CCN(C)CC 1 620 610
2 N Tertiary_aliph_amine CCN(C)CC 1 620 610
3 C Primary_carbon CCN(C)CC 1 620 610
4 C Primary_carbon CCN(C)CC 1 620 610
5 C NA CCN(C)CC 1 620 610
11 C Primary_carbon C 2 620 610
16 C Primary_carbon C 3 620 610
0 C Acetal CO 1 730 611
1 O Acetal, Acetal_like CO 1 730 611
0 C Alkylarylether CO 1 1014 612
1 O Alkylarylether CO 1 1014 612
8 O Phenol O 2 1014 612
10 C Alkene, Conjugated_double_bond CC(=O)O 3 1014 612
11 C Carboxylic_acid, Conjugated_double_bond CC(=O)O 3 1014 612
12 O Carboxylic_acid, Conjugated_double_bond CC(=O)O 3 1014 612
13 O Carboxylic_acid CC(=O)O 3 1014 612
0 C Primary_carbon C 1 937 613
11 O Alkylarylether CO 2 937 613
12 C Alkylarylether CO 2 937 613
14 C Alkylarylether C 3 937 613
0 C Aromatic cccc 1 786 614
1 C Aromatic cccc 1 786 614
2 C Aromatic cccc 1 786 614
5 C Aromatic cccc 1 786 614
9 C Carboxylic_acid, Alpha_aminoacid O=CO 2 786 614
10 O Carboxylic_acid, Alpha_aminoacid O=CO 2 786 614
11 O Carboxylic_acid, Alpha_aminoacid O=CO 2 786 614
12 N Primary_aliph_amine, Alpha_aminoacid N 3 786 614
0 C Primary_carbon CC 1 980 617
1 C Primary_carbon, Alkene CC 1 980 617
4 C Tertiary_carbon, Alkene C=C(C)C 2 980 617
5 C Primary_carbon, Secondary_carbon, Alkene C=C(C)C 2 980 617
6 C Primary_carbon C=C(C)C 2 980 617
7 C Secondary_carbon C=C(C)C 2 980 617
10 C Aromatic, Conjugated_double_bond ccc([nH])=O 3 980 617
11 C Lactam, Aromatic, Conjugated_double_bond ccc([nH])=O 3 980 617
12 C Lactam, Oxoarene, Aromatic, Conjugated_double_bond ccc([nH])=O 3 980 617
13 O Lactam, Oxoarene, Conjugated_double_bond ccc([nH])=O 3 980 617
14 N Lactam, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond ccc([nH])=O 3 980 617
19 Cl Arylchloride Cl 1 749 618
20 Cl Arylchloride Cl 2 749 618
0 C Primary_carbon, Secondary_carbon C 1 707 620
5 C Primary_carbon C 2 707 620
13 I Aryliodide I 1 881 621
0 C Primary_carbon C 1 631 622
13 C Carboxylic_ester C 2 631 622
4 C Secondary_carbon, Tertiary_carbon C 1 815 623
12 S NA S 2 815 623
13 S NA S 3 815 623
14 O Ketone, Conjugated_double_bond O 1 890 627
17 C Aromatic, Conjugated_double_bond ccs 2 890 627
18 C Aromatic ccs 2 890 627
19 S Hetero_S, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond ccs 2 890 627
3 C Aromatic cccc 1 642 629
4 C Aromatic cccc 1 642 629
5 C Aromatic cccc 1 642 629
6 C Aromatic cccc 1 642 629
10 C Aromatic, Annelated_rings c1ccccc1 2 642 629
11 C Aromatic c1ccccc1 2 642 629
12 C Aromatic c1ccccc1 2 642 629
13 C Aromatic c1ccccc1 2 642 629
14 C Aromatic c1ccccc1 2 642 629
15 C Aromatic, Annelated_rings c1ccccc1 2 642 629
0 C Secondary_carbon CCC 1 815 630
1 C Secondary_carbon, Tertiary_carbon CCC 1 815 630
4 C Secondary_carbon, Tertiary_carbon C 2 815 630
7 C Secondary_carbon, Tertiary_carbon CCC 1 815 630
12 S NA S 3 815 630
13 S NA S 4 815 630
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 634
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 634
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 634
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 634
9 C Nitrile, Conjugated_double_bond, Conjugated_tripple_bond C#N 2 782 634
10 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond C#N 2 782 634
11 C Thioamide, Conjugated_double_bond NC=S 3 782 634
12 S Thioamide, Conjugated_double_bond NC=S 3 782 634
13 N Thioamide NC=S 3 782 634
17 O Phenol O 4 782 634
18 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 634
19 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 634
20 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 634
21 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 634
0 C Primary_carbon C 1 653 635
0 C Alkyne C#CC 1 716 639
1 C Alkyne C#CC 1 716 639
2 C NA C#CC 1 716 639
4 C NA C 2 716 639
0 C Primary_carbon, Tertiary_carbon C 1 855 641
23 N Tertiary_aliph_amine CNC 2 855 641
24 C NA CNC 2 855 641
25 C NA CNC 2 855 641
28 O Secondary_alcohol O 3 855 641
0 C Alkene, Conjugated_double_bond C 1 957 642
7 C Quaternary_carbon, Hemiacetal CO 2 957 642
8 O Hemiacetal, Acetal_like, Heterocyclic, Sugar_pattern_2, Sugar_pattern_2_reducing CO 2 957 642
14 C Primary_carbon, Quaternary_carbon C 3 957 642
18 O Secondary_alcohol O 4 957 642
19 O Secondary_alcohol O 5 957 642
22 O Ketone, Conjugated_double_bond O 6 957 642
23 C Tertiary_carbon, Quaternary_carbon, Secondary_alcohol CO 7 957 642
24 O Secondary_alcohol CO 7 957 642
25 O Hemiacetal, Acetal_like O 8 957 642
9 O Phenol, 1,2-Diphenol O 1 668 645
11 C Secondary_carbon, Tertiary_carbon CCC=O 1 952 646
12 C Secondary_carbon, Ketone, CH-acidic CCC=O 1 952 646
13 C Secondary_carbon, Quaternary_carbon, Ketone CCC=O 1 952 646
14 O Ketone CCC=O 1 952 646
16 C Primary_carbon, Quaternary_carbon C 2 952 646
20 O Secondary_alcohol O 3 952 646
8 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl F 1 737 647
9 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl F 2 737 647
10 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl F 3 737 647
11 S Isothiourea, Hetero_S, Heteroaromatic, Aromatic, Heterocyclic nc(N)s 4 737 647
12 C Primary_arom_amine, Isothiourea, Aromatic nc(N)s 4 737 647
13 N Primary_arom_amine, Isothiourea nc(N)s 4 737 647
14 N Isothiourea, Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nc(N)s 4 737 647
0 C Primary_carbon, Secondary_carbon CCCCC 1 720 648
1 C Primary_carbon, Secondary_carbon CCCCC 1 720 648
2 C Secondary_carbon CCCCC 1 720 648
3 C Secondary_carbon CCCCC 1 720 648
4 C Secondary_carbon CCCCC 1 720 648
14 N Tertiary_aliph_amine, Heterocyclic C1COCCN1 2 720 648
15 C NA C1COCCN1 2 720 648
16 C Dialkylether C1COCCN1 2 720 648
17 O Dialkylether, Heterocyclic C1COCCN1 2 720 648
18 C Dialkylether C1COCCN1 2 720 648
19 C NA C1COCCN1 2 720 648
21 C Aromatic c1ccccc1 3 720 648
22 C Aromatic c1ccccc1 3 720 648
23 C Aromatic c1ccccc1 3 720 648
24 C Aromatic c1ccccc1 3 720 648
25 C Aromatic c1ccccc1 3 720 648
26 C Aromatic c1ccccc1 3 720 648
27 O Secondary_alcohol O 4 720 648
0 C NA CNC 1 667 649
1 N Tertiary_aliph_amine CNC 1 667 649
2 C NA CNC 1 667 649
6 C NA Cc1cccs1 2 667 649
7 C Aromatic Cc1cccs1 2 667 649
8 C Aromatic Cc1cccs1 2 667 649
9 C Aromatic Cc1cccs1 2 667 649
10 C Aromatic Cc1cccs1 2 667 649
11 S Hetero_S, Heteroaromatic, Aromatic, Heterocyclic Cc1cccs1 2 667 649
12 C Imidolactam, Aromatic c1ccncc1 3 667 649
13 C Imidolactam, Aromatic c1ccncc1 3 667 649
14 C Aromatic c1ccncc1 3 667 649
15 C Aromatic c1ccncc1 3 667 649
16 C Aromatic c1ccncc1 3 667 649
17 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 3 667 649
0 C Primary_carbon C 1 785 652
13 C Secondary_carbon CCCN 2 785 652
14 C Secondary_carbon CCCN 2 785 652
15 C Secondary_carbon CCCN 2 785 652
16 N Primary_aliph_amine CCCN 2 785 652
17 C Ketone O=CCCl 3 785 652
18 O Ketone O=CCCl 3 785 652
19 C Alkylchloride, Ketone O=CCCl 3 785 652
20 Cl Alkylchloride O=CCCl 3 785 652
10 O Carboxylic_acid, Alpha_aminoacid O 1 786 653
11 O Carboxylic_acid, Alpha_aminoacid O 2 786 653
0 C Primary_carbon, Secondary_carbon CCC 1 707 655
1 C Primary_carbon, Secondary_carbon CCC 1 707 655
2 C Secondary_carbon CCC 1 707 655
15 C Primary_carbon C 2 707 655
0 C Primary_carbon C 1 827 656
6 C Primary_carbon C 2 827 656
14 C Primary_carbon, Quaternary_carbon CC(C)C 3 827 656
15 C Primary_carbon, Quaternary_carbon CC(C)C 3 827 656
16 C Primary_carbon, Quaternary_carbon CC(C)C 3 827 656
17 C Primary_carbon, Quaternary_carbon CC(C)C 3 827 656
0 C Secondary_carbon, Tertiary_carbon C1CC1 1 666 657
1 C Secondary_carbon, Tertiary_carbon C1CC1 1 666 657
2 C Secondary_carbon, Tertiary_carbon C1CC1 1 666 657
16 N Primary_arom_amine N 1 702 658
0 C Primary_carbon C 1 950 661
7 C Carboxylic_acid, Conjugated_double_bond O=CO 2 950 661
8 O Carboxylic_acid, Conjugated_double_bond O=CO 2 950 661
9 O Carboxylic_acid O=CO 2 950 661
10 O Phenol O 3 950 661
11 O Phenol O 4 950 661
21 O Acetal, Acetal_like, Heterocyclic OCO 1 936 662
22 C Acetal, Acetal_like OCO 1 936 662
23 O Acetal, Acetal_like, Heterocyclic OCO 1 936 662
13 C Quaternary_carbon, Aromatic c1ccncc1 1 853 664
14 C Aromatic c1ccncc1 1 853 664
15 C Aromatic c1ccncc1 1 853 664
16 C Aromatic c1ccncc1 1 853 664
17 C Aromatic c1ccncc1 1 853 664
18 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1ccncc1 1 853 664
19 C Quaternary_carbon, Primary_amide NC=O 2 853 664
20 O Primary_amide NC=O 2 853 664
21 N Primary_amide NC=O 2 853 664
23 C Primary_carbon C 3 853 664
24 C Primary_carbon C 4 853 664
0 C Primary_carbon CCC 1 881 668
1 C Primary_carbon CCC 1 881 668
2 C Primary_carbon CCC 1 881 668
13 I Aryliodide I 2 881 668
7 C Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl FC(F)F 1 737 669
8 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl FC(F)F 1 737 669
9 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl FC(F)F 1 737 669
10 F Alkylfluoride, Halogen_acetal_like, Acetal_like, Trifluoromethyl FC(F)F 1 737 669
11 S Isothiourea, Hetero_S, Heteroaromatic, Aromatic, Heterocyclic nc(N)s 2 737 669
12 C Primary_arom_amine, Isothiourea, Aromatic nc(N)s 2 737 669
13 N Primary_arom_amine, Isothiourea nc(N)s 2 737 669
14 N Isothiourea, Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic nc(N)s 2 737 669
0 C Primary_carbon, Secondary_carbon CCCN 1 707 670
1 C Primary_carbon, Secondary_carbon CCCN 1 707 670
2 C Secondary_carbon CCCN 1 707 670
3 N Secondary_aliph_amine CCCN 1 707 670
7 O Secondary_amide O 2 707 670
0 C Primary_carbon CCNCC 1 771 674
1 C Primary_carbon CCNCC 1 771 674
2 N Tertiary_aliph_amine CCNCC 1 771 674
3 C Primary_carbon CCNCC 1 771 674
4 C Primary_carbon CCNCC 1 771 674
16 O Alkylarylether CO 2 771 674
17 C Alkylarylether CO 2 771 674
18 N Primary_arom_amine N 3 771 674
19 Cl Arylchloride Cl 4 771 674
14 O Ketone O 1 952 676
0 C Primary_carbon, Secondary_carbon CC 1 860 680
1 C Primary_carbon, Secondary_carbon CC 1 860 680
0 C Alkene C=CC 1 767 681
1 C Alkene C=CC 1 767 681
2 C NA C=CC 1 767 681
7 C Aromatic cc(O)c(c)O 2 767 681
8 C Phenol, 1,2-Diphenol, Aromatic cc(O)c(c)O 2 767 681
9 C Phenol, 1,2-Diphenol, Aromatic cc(O)c(c)O 2 767 681
10 C Aromatic cc(O)c(c)O 2 767 681
14 C Tertiary_carbon, Aromatic c1ccccc1 3 767 681
15 C Aromatic c1ccccc1 3 767 681
16 C Aromatic c1ccccc1 3 767 681
17 C Aromatic c1ccccc1 3 767 681
18 C Aromatic c1ccccc1 3 767 681
19 C Aromatic c1ccccc1 3 767 681
20 O Phenol, 1,2-Diphenol cc(O)c(c)O 2 767 681
21 O Phenol, 1,2-Diphenol cc(O)c(c)O 2 767 681
0 C Enolether CO 1 851 684
1 O Enolether CO 1 851 684
5 O Ketone, Conjugated_double_bond O 2 851 684
13 O Ketone, Conjugated_double_bond O 3 851 684
14 O Enolether CO 4 851 684
15 C Enolether CO 4 851 684
22 O Secondary_alcohol, 1,2-Diol O 1 959 686
0 C Primary_carbon, Secondary_carbon C 1 698 688
13 C Aromatic cn[nH] 2 698 688
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cn[nH] 2 698 688
15 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic cn[nH] 2 698 688
0 C Aromatic cccc 1 691 689
1 C Aromatic cccc 1 691 689
2 C Aromatic, Conjugated_double_bond cccc 1 691 689
5 C Aromatic, Conjugated_double_bond cccc 1 691 689
7 O Alkyl_imide, Conjugated_double_bond O 2 691 689
11 C Secondary_carbon CC(=O)O 3 691 689
12 C Secondary_carbon, Carboxylic_acid CC(=O)O 3 691 689
13 O Carboxylic_acid CC(=O)O 3 691 689
14 O Carboxylic_acid CC(=O)O 3 691 689
15 C Carboxylic_acid O=CO 4 691 689
16 O Carboxylic_acid O=CO 4 691 689
17 O Carboxylic_acid O=CO 4 691 689
13 C Aromatic cccc 1 717 690
14 C Aromatic cccc 1 717 690
15 C Aromatic cccc 1 717 690
16 C Aromatic cccc 1 717 690
27 N Primary_arom_amine N 1 837 693
14 O Lactam, Oxoarene, Conjugated_double_bond O 1 701 695
0 C Primary_carbon, Secondary_carbon CCC 1 698 696
1 C Primary_carbon, Secondary_carbon CCC 1 698 696
2 C Secondary_carbon CCC 1 698 696
13 C Aromatic cn[nH] 2 698 696
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cn[nH] 2 698 696
15 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic cn[nH] 2 698 696
0 C Primary_carbon, Secondary_carbon CCCNCC 1 707 697
1 C Primary_carbon, Secondary_carbon CCCNCC 1 707 697
2 C Secondary_carbon CCCNCC 1 707 697
3 N Secondary_aliph_amine CCCNCC 1 707 697
4 C Primary_carbon CCCNCC 1 707 697
5 C Primary_carbon CCCNCC 1 707 697
7 O Secondary_amide O 2 707 697
15 C Primary_carbon C 3 707 697
7 O Oxoarene, Conjugated_double_bond O 1 896 698
10 C Carboxylic_acid, Conjugated_double_bond O=CO 2 896 698
11 O Carboxylic_acid, Conjugated_double_bond O=CO 2 896 698
12 O Carboxylic_acid O=CO 2 896 698
21 F Alkylfluoride, Trifluoromethyl F 1 768 699
22 F Alkylfluoride, Trifluoromethyl F 2 768 699
23 F Alkylfluoride, Trifluoromethyl F 3 768 699
0 C NA C 1 862 701
5 C Aromatic ccc 2 862 701
6 C Aromatic ccc 2 862 701
7 C Aromatic ccc 2 862 701
15 O Phenol O 3 862 701
16 O Alkylarylether CO 4 862 701
17 C Alkylarylether CO 4 862 701
16 O Alkylarylether CO 1 758 702
17 C Alkylarylether CO 1 758 702
18 S Sulfon, Conjugated_double_bond C[SH](=O)=O 2 758 702
19 O Conjugated_double_bond C[SH](=O)=O 2 758 702
20 O Conjugated_double_bond C[SH](=O)=O 2 758 702
21 C CH-acidic C[SH](=O)=O 2 758 702
0 C Alkylarylether C 1 718 705
19 N Primary_arom_amine N 2 718 705
0 C Tertiary_amide C 1 796 707
6 C Secondary_carbon CCCO 2 796 707
7 C Secondary_carbon CCCO 2 796 707
8 C Secondary_carbon, Dialkylether CCCO 2 796 707
9 O Dialkylether, Heterocyclic CCCO 2 796 707
12 N Tertiary_aliph_amine, Heterocyclic C1CCNC1 3 796 707
13 C Secondary_carbon C1CCNC1 3 796 707
14 C Secondary_carbon C1CCNC1 3 796 707
15 C Secondary_carbon C1CCNC1 3 796 707
16 C Secondary_carbon C1CCNC1 3 796 707
20 C Secondary_carbon, Aromatic c1ccccc1 4 796 707
21 C Aromatic c1ccccc1 4 796 707
22 C Aromatic c1ccccc1 4 796 707
23 C Aromatic c1ccccc1 4 796 707
24 C Aromatic c1ccccc1 4 796 707
25 C Aromatic c1ccccc1 4 796 707
6 C Secondary_carbon CCCO 1 796 708
7 C Secondary_carbon CCCO 1 796 708
8 C Secondary_carbon, Dialkylether CCCO 1 796 708
9 O Dialkylether, Heterocyclic CCCO 1 796 708
12 N Tertiary_aliph_amine, Heterocyclic C1CCNC1 2 796 708
13 C Secondary_carbon C1CCNC1 2 796 708
14 C Secondary_carbon C1CCNC1 2 796 708
15 C Secondary_carbon C1CCNC1 2 796 708
16 C Secondary_carbon C1CCNC1 2 796 708
18 O Tertiary_amide O 3 796 708
0 C Primary_carbon, Secondary_carbon CCC 1 715 711
1 C Primary_carbon, Secondary_carbon CCC 1 715 711
2 C Secondary_carbon CCC 1 715 711
13 C Aromatic cnc(n)N 2 715 711
14 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cnc(n)N 2 715 711
15 C Primary_arom_amine, Aromatic cnc(n)N 2 715 711
16 N Primary_arom_amine cnc(n)N 2 715 711
17 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic cnc(n)N 2 715 711
7 O Oxoarene, Conjugated_double_bond O 1 896 715
10 C Carboxylic_acid, Conjugated_double_bond O=CO 2 896 715
11 O Carboxylic_acid, Conjugated_double_bond O=CO 2 896 715
12 O Carboxylic_acid O=CO 2 896 715
14 C Secondary_carbon CCOC 1 903 717
15 C Secondary_carbon, Dialkylether CCOC 1 903 717
16 O Dialkylether CCOC 1 903 717
17 C Dialkylether CCOC 1 903 717
7 O Phenol, 1,2-Diphenol O 1 933 718
8 O Phenol, 1,2-Diphenol O 2 933 718
20 O Phenol O 3 933 718
21 O Phenol O 4 933 718
22 C Alkylfluoride, Trifluoromethyl FC(F)F 1 813 721
23 F Alkylfluoride, Trifluoromethyl FC(F)F 1 813 721
24 F Alkylfluoride, Trifluoromethyl FC(F)F 1 813 721
25 F Alkylfluoride, Trifluoromethyl FC(F)F 1 813 721
0 C Primary_carbon CC 1 867 723
1 C Primary_carbon, Alkene, Conjugated_double_bond CC 1 867 723
4 O Ketone, Conjugated_double_bond O 2 867 723
0 C Alkylarylether CO 1 935 725
1 O Alkylarylether CO 1 935 725
16 O Phenol O 2 935 725
0 C Alkene C=CC 1 992 730
1 C Primary_carbon, Alkene C=CC 1 992 730
2 C Primary_carbon C=CC 1 992 730
10 C Aromatic, Conjugated_double_bond ccc(=O)o 2 992 730
11 C Lactone, Aromatic, Conjugated_double_bond ccc(=O)o 2 992 730
12 C Lactone, Oxoarene, Aromatic, Conjugated_double_bond ccc(=O)o 2 992 730
13 O Lactone, Oxoarene, Conjugated_double_bond ccc(=O)o 2 992 730
14 O Lactone, Hetero_O, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond ccc(=O)o 2 992 730
3 C Primary_carbon C 1 751 731
13 C Primary_alcohol CO 2 751 731
14 O Primary_alcohol CO 2 751 731
15 O Phenol O 3 751 731
0 C Secondary_carbon CCC 1 815 737
1 C Secondary_carbon, Tertiary_carbon CCC 1 815 737
4 C Secondary_carbon, Tertiary_carbon C 2 815 737
7 C Secondary_carbon, Tertiary_carbon CCC 1 815 737
12 S NA S 3 815 737
13 S NA S 4 815 737
19 C Alkylarylether C 1 765 739
21 C Alkylarylether C 2 765 739
8 N Tertiary_mixed_amine, Heterocyclic C1CNCCN1 1 756 742
9 C NA C1CNCCN1 1 756 742
10 C NA C1CNCCN1 1 756 742
11 N Secondary_aliph_amine, Heterocyclic C1CNCCN1 1 756 742
12 C NA C1CNCCN1 1 756 742
13 C NA C1CNCCN1 1 756 742
19 S Sulfonamide, Conjugated_double_bond N[SH](=O)=O 1 750 749
20 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 1 750 749
21 O Sulfonamide, Conjugated_double_bond N[SH](=O)=O 1 750 749
22 N Sulfonamide N[SH](=O)=O 1 750 749
13 O Phenol O 1 760 751
14 O Phenol O 2 760 751
6 C Alkylfluoride, Trifluoromethyl FC(F)F 1 792 756
7 F Alkylfluoride, Trifluoromethyl FC(F)F 1 792 756
8 F Alkylfluoride, Trifluoromethyl FC(F)F 1 792 756
9 F Alkylfluoride, Trifluoromethyl FC(F)F 1 792 756
10 N Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic c1cncn1 2 792 756
11 C Aromatic c1cncn1 2 792 756
12 C Aromatic c1cncn1 2 792 756
13 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1cncn1 2 792 756
14 C Aromatic c1cncn1 2 792 756
0 C Primary_carbon CC(C)N 1 881 759
1 C Primary_carbon CC(C)N 1 881 759
2 C Primary_carbon CC(C)N 1 881 759
3 N Secondary_aliph_amine CC(C)N 1 881 759
13 I Aryliodide I 2 881 759
13 Cl Arylchloride Cl 1 769 760
0 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 762
1 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 762
2 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 762
3 C Primary_carbon, Quaternary_carbon CC(C)C 1 782 762
10 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N 2 782 762
11 C Thioamide, Conjugated_double_bond NC=S 3 782 762
12 S Thioamide, Conjugated_double_bond NC=S 3 782 762
13 N Thioamide NC=S 3 782 762
17 O Phenol O 4 782 762
18 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 762
19 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 762
20 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 762
21 C Primary_carbon, Quaternary_carbon CC(C)C 5 782 762
17 Cl Arylchloride Cl 1 776 765
0 C Primary_carbon, Quaternary_carbon C 1 909 766
2 C Primary_carbon, Quaternary_carbon C 2 909 766
7 C Primary_carbon, Quaternary_carbon C 3 909 766
12 C Primary_carbon C 4 909 766
14 C Secondary_carbon, Tertiary_carbon, Lactone, CH-acidic CC(=O)O 5 909 766
15 C Secondary_carbon, Lactone CC(=O)O 5 909 766
16 O Lactone CC(=O)O 5 909 766
17 O Lactone, Heterocyclic CC(=O)O 5 909 766
12 Cl Arylchloride Cl 1 848 767
5 C Primary_carbon C 1 881 769
13 I Aryliodide I 2 881 769
0 C Primary_carbon, Secondary_carbon CCCC 1 800 771
1 C Primary_carbon, Secondary_carbon CCCC 1 800 771
2 C Secondary_carbon CCCC 1 800 771
3 C Secondary_carbon CCCC 1 800 771
12 C Secondary_carbon CCCCN 1 785 772
13 C Secondary_carbon CCCCN 1 785 772
14 C Secondary_carbon CCCCN 1 785 772
15 C Secondary_carbon CCCCN 1 785 772
16 N Primary_aliph_amine CCCCN 1 785 772
17 C Ketone O=CCCl 2 785 772
18 O Ketone O=CCCl 2 785 772
19 C Alkylchloride, Ketone O=CCCl 2 785 772
20 Cl Alkylchloride O=CCCl 2 785 772
13 C Secondary_carbon CCCN 1 785 774
14 C Secondary_carbon CCCN 1 785 774
15 C Secondary_carbon CCCN 1 785 774
16 N Primary_aliph_amine CCCN 1 785 774
0 C Primary_carbon, Tertiary_carbon CC(C)CCN 1 878 778
1 C Primary_carbon, Secondary_carbon, Tertiary_carbon CC(C)CCN 1 878 778
2 C Primary_carbon, Tertiary_carbon CC(C)CCN 1 878 778
3 C Secondary_carbon, Tertiary_carbon CC(C)CCN 1 878 778
4 C Secondary_carbon CC(C)CCN 1 878 778
9 C Secondary_carbon CC(C)CCN 2 878 778
10 C Secondary_carbon, Tertiary_carbon CC(C)CCN 2 878 778
11 C Primary_carbon, Secondary_carbon, Tertiary_carbon CC(C)CCN 2 878 778
12 C Primary_carbon, Tertiary_carbon CC(C)CCN 2 878 778
13 C Primary_carbon, Tertiary_carbon CC(C)CCN 2 878 778
14 N Primary_aliph_amine CC(C)CCN 2 878 778
15 N Primary_aliph_amine CC(C)CCN 1 878 778
13 O Phenol, 1,2-Diphenol O 1 805 782
15 O Ketone O 1 975 784
0 C Primary_carbon CC=O 1 832 786
1 C Primary_carbon, Secondary_amide CC=O 1 832 786
2 O Secondary_amide CC=O 1 832 786
0 C Primary_carbon CC 1 840 791
1 C Primary_carbon CC 1 840 791
3 C Primary_carbon CCC 2 840 791
4 C Primary_carbon CCC 2 840 791
5 C Primary_carbon CCC 2 840 791
8 Cl Imidoylhalide_cyclic, Arylchloride Cl 3 840 791
12 N Primary_arom_amine N 4 840 791
14 C Conjugated_double_bond NC(N)=NC=O 5 840 791
15 O Conjugated_double_bond NC(N)=NC=O 5 840 791
16 N Guanidine, Conjugated_double_bond NC(N)=NC=O 5 840 791
17 C Guanidine, Conjugated_double_bond NC(N)=NC=O 5 840 791
18 N Guanidine NC(N)=NC=O 5 840 791
19 N Guanidine NC(N)=NC=O 5 840 791
0 C Secondary_carbon CCC 1 815 792
1 C Secondary_carbon, Tertiary_carbon CCC 1 815 792
4 C Secondary_carbon, Tertiary_carbon C 2 815 792
7 C Secondary_carbon, Tertiary_carbon CCC 1 815 792
10 O NA OC(=S)S 3 815 792
11 C NA OC(=S)S 3 815 792
12 S NA OC(=S)S 3 815 792
13 S NA OC(=S)S 3 815 792
0 C Primary_carbon, Tertiary_carbon C 1 911 793
6 C Primary_carbon, Quaternary_carbon C 2 911 793
7 C Primary_carbon, Quaternary_carbon C 3 911 793
11 O Carboxylic_ester, Conjugated_double_bond O 4 911 793
18 O Phenol O 5 911 793
9 N Nitrile, Conjugated_double_bond, Conjugated_tripple_bond N 1 805 794
10 C Thioamide, Conjugated_double_bond NC=S 2 805 794
11 S Thioamide, Conjugated_double_bond NC=S 2 805 794
12 N Thioamide NC=S 2 805 794
13 O Phenol, 1,2-Diphenol O 3 805 794
26 Cl Arylchloride Cl 1 809 796
27 Cl Arylchloride Cl 2 809 796
0 C NA C 1 885 799
0 C Primary_carbon CNC(C)C 1 894 800
1 C Primary_carbon CNC(C)C 1 894 800
2 C Primary_carbon CNC(C)C 1 894 800
3 N Secondary_aliph_amine, 1,2-Aminoalcohol CNC(C)C 1 894 800
4 C 1,2-Aminoalcohol CNC(C)C 1 894 800
12 O Phenol, 1,2-Diphenol O 2 894 800
13 O Phenol, 1,2-Diphenol O 3 894 800
0 C Alkylarylether C 1 1014 805
12 O Carboxylic_acid, Conjugated_double_bond O 2 1014 805
13 O Carboxylic_acid O 3 1014 805
0 C Primary_carbon C 1 950 815
7 C Carboxylic_acid, Conjugated_double_bond O=CO 2 950 815
8 O Carboxylic_acid, Conjugated_double_bond O=CO 2 950 815
9 O Carboxylic_acid O=CO 2 950 815
10 O Phenol O 3 950 815
0 C Primary_carbon C 1 820 818
6 C Primary_carbon C 2 820 818
9 C Isothiourea C1=NCCCS1 3 820 818
10 N Isothiourea, Heterocyclic C1=NCCCS1 3 820 818
11 C Secondary_carbon C1=NCCCS1 3 820 818
12 C Secondary_carbon C1=NCCCS1 3 820 818
13 C Secondary_carbon C1=NCCCS1 3 820 818
14 S Isothiourea, Heterocyclic C1=NCCCS1 3 820 818
0 C Primary_carbon CC 1 980 820
1 C Primary_carbon, Alkene CC 1 980 820
4 C Tertiary_carbon, Alkene C=C(C)C 2 980 820
5 C Primary_carbon, Secondary_carbon, Alkene C=C(C)C 2 980 820
6 C Primary_carbon C=C(C)C 2 980 820
7 C Secondary_carbon C=C(C)C 2 980 820
10 C Aromatic, Conjugated_double_bond ccc([nH])=O 3 980 820
11 C Lactam, Aromatic, Conjugated_double_bond ccc([nH])=O 3 980 820
12 C Lactam, Oxoarene, Aromatic, Conjugated_double_bond ccc([nH])=O 3 980 820
13 O Lactam, Oxoarene, Conjugated_double_bond ccc([nH])=O 3 980 820
14 N Lactam, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond ccc([nH])=O 3 980 820
0 C Primary_carbon C 1 829 825
8 O Carboxylic_acid, Conjugated_double_bond O 1 950 827
9 O Carboxylic_acid O 2 950 827
10 O Phenol O 3 950 827
11 O Phenol O 4 950 827
0 C Alkylarylether CO 1 835 831
1 O Alkylarylether CO 1 835 831
9 O Alkyl_imide, Conjugated_double_bond O 2 835 831
10 N Alkyl_imide, Heterocyclic O=C1CCCN1 3 835 831
11 C Secondary_carbon, Alkyl_imide O=C1CCCN1 3 835 831
12 C Secondary_carbon O=C1CCCN1 3 835 831
13 C Secondary_carbon, CH-acidic O=C1CCCN1 3 835 831
14 C Secondary_carbon, Alkyl_imide O=C1CCCN1 3 835 831
15 O Alkyl_imide O=C1CCCN1 3 835 831
15 O Phenol O 1 839 832
7 C Quaternary_carbon, Hemiacetal CO 1 957 834
8 O Hemiacetal, Acetal_like, Heterocyclic, Sugar_pattern_2, Sugar_pattern_2_reducing CO 1 957 834
13 C Primary_carbon, Quaternary_carbon C 2 957 834
14 C Primary_carbon, Quaternary_carbon C 3 957 834
18 O Secondary_alcohol O 4 957 834
19 O Secondary_alcohol O 5 957 834
22 O Ketone, Conjugated_double_bond O 6 957 834
23 C Tertiary_carbon, Quaternary_carbon, Secondary_alcohol CO 7 957 834
24 O Secondary_alcohol CO 7 957 834
25 O Hemiacetal, Acetal_like O 8 957 834
0 C Primary_carbon CCS(N)(=O)=O 1 845 835
1 C Primary_carbon CCS(N)(=O)=O 1 845 835
2 S Sulfonamide CCS(N)(=O)=O 1 845 835
3 O Sulfonamide CCS(N)(=O)=O 1 845 835
4 O Sulfonamide CCS(N)(=O)=O 1 845 835
5 N Sulfonamide CCS(N)(=O)=O 1 845 835
13 C Secondary_carbon, Alkene, Conjugated_double_bond C1CCCCC1 2 845 835
14 C Secondary_carbon C1CCCCC1 2 845 835
15 C Secondary_carbon C1CCCCC1 2 845 835
16 C Secondary_carbon C1CCCCC1 2 845 835
17 C Secondary_carbon C1CCCCC1 2 845 835
18 C Secondary_carbon C1CCCCC1 2 845 835
19 C Aromatic, Conjugated_double_bond c1c[nH]cn1 3 845 835
20 C Aromatic, Conjugated_double_bond c1c[nH]cn1 3 845 835
21 N Hetero_N_nonbasic, Heteroaromatic, Aromatic, Heterocyclic c1c[nH]cn1 3 845 835
22 C Aromatic c1c[nH]cn1 3 845 835
23 N Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond c1c[nH]cn1 3 845 835
0 C NA C 1 900 836
0 C NA C[N+]C 1 843 838
1 N Quaternary_aliph_ammonium, Ammonium, Heterocyclic, Kation C[N+]C 1 843 838
2 C NA C[N+]C 1 843 838
0 C Primary_carbon, Tertiary_carbon C 1 841 840
2 C Primary_carbon, Tertiary_carbon C 2 841 840
0 C Aromatic cc(Cl)c(c)Cl 1 861 841
1 C Arylchloride, Aromatic cc(Cl)c(c)Cl 1 861 841
2 C Arylchloride, Aromatic cc(Cl)c(c)Cl 1 861 841
3 C Aromatic cc(Cl)c(c)Cl 1 861 841
8 O Lactam, Oxoarene, Conjugated_double_bond O 2 861 841
10 O Lactam, Oxoarene, Conjugated_double_bond O 3 861 841
12 Cl Arylchloride cc(Cl)c(c)Cl 1 861 841
13 Cl Arylchloride cc(Cl)c(c)Cl 1 861 841
0 C NA CN 1 1008 842
1 N Secondary_aliph_amine CN 1 1008 842
4 C Aromatic ccccc 2 1008 842
5 C Aromatic ccccc 2 1008 842
6 C Aromatic ccccc 2 1008 842
7 C Aromatic ccccc 2 1008 842
8 C Aromatic ccccc 2 1008 842
18 C Tertiary_carbon, Aromatic c1ccccc1 1 856 843
19 C Aromatic c1ccccc1 1 856 843
20 C Aromatic c1ccccc1 1 856 843
21 C Aromatic c1ccccc1 1 856 843
22 C Aromatic c1ccccc1 1 856 843
23 C Aromatic c1ccccc1 1 856 843
0 C Primary_carbon C 1 950 844
7 C Carboxylic_acid, Conjugated_double_bond O=CO 2 950 844
8 O Carboxylic_acid, Conjugated_double_bond O=CO 2 950 844
9 O Carboxylic_acid O=CO 2 950 844
10 O Phenol O 3 950 844
11 O Phenol O 4 950 844
0 C Secondary_carbon C1CCNCC1 1 850 845
1 C Secondary_carbon C1CCNCC1 1 850 845
2 C Secondary_carbon, Tertiary_amide C1CCNCC1 1 850 845
3 N Tertiary_amide, Heterocyclic C1CCNCC1 1 850 845
4 C Secondary_carbon, Tertiary_amide C1CCNCC1 1 850 845
5 C Secondary_carbon C1CCNCC1 1 850 845
7 O Tertiary_amide, Conjugated_double_bond O 2 850 845
14 O Alkylarylether, Heterocyclic OCCO 3 850 845
15 C Alkylarylether OCCO 3 850 845
16 C Alkylarylether OCCO 3 850 845
17 O Alkylarylether, Heterocyclic OCCO 3 850 845
0 C Primary_carbon, Tertiary_carbon CCC(=O)O 1 875 850
1 C Primary_carbon, Tertiary_carbon CCC(=O)O 1 875 850
10 C Ketone, Aromatic, Conjugated_double_bond c1ccccc1 2 875 850
11 C Aromatic, Conjugated_double_bond c1ccccc1 2 875 850
12 C Aromatic c1ccccc1 2 875 850
13 C Aromatic c1ccccc1 2 875 850
14 C Aromatic c1ccccc1 2 875 850
15 C Aromatic, Conjugated_double_bond c1ccccc1 2 875 850
16 C Tertiary_carbon, Carboxylic_acid CCC(=O)O 1 875 850
17 O Carboxylic_acid CCC(=O)O 1 875 850
18 O Carboxylic_acid CCC(=O)O 1 875 850
0 C Primary_carbon CCC(C)(C)O 1 897 851
1 C Primary_carbon, Secondary_carbon, Enolether CCC(C)(C)O 1 897 851
2 C Primary_carbon CCC(C)(C)O 1 897 851
3 C Secondary_carbon CCC(C)(C)O 1 897 851
4 C Secondary_carbon CCC(C)(C)O 1 897 851
14 O Ketone, Conjugated_double_bond O 2 897 851
17 O Enolether, Heterocyclic CCC(C)(C)O 1 897 851
0 C Alkyne C 1 865 860
0 C Primary_carbon CCnc([nH])=O 1 868 861
1 C Primary_carbon CCnc([nH])=O 1 868 861
2 N Urea, Hetero_N_basic_no_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond CCnc([nH])=O 1 868 861
9 N Urea, Hetero_N_basic_H, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond CCnc([nH])=O 1 868 861
10 C Urea, Oxoarene, Aromatic, Conjugated_double_bond CCnc([nH])=O 1 868 861
11 O Urea, Oxoarene, Conjugated_double_bond CCnc([nH])=O 1 868 861
0 C Primary_carbon, Secondary_carbon CC 1 869 862
1 C Primary_carbon, Secondary_carbon CC 1 869 862
0 C Primary_carbon, Ketone, CH-acidic CC=O 1 971 867
1 C Primary_carbon, Ketone CC=O 1 971 867
2 O Ketone CC=O 1 971 867
16 C Primary_carbon, Quaternary_carbon C 2 971 867
21 C Primary_carbon, Quaternary_carbon C 3 971 867
22 O Carboxylic_ester CC(=O)O 4 971 867
23 C Primary_carbon, Carboxylic_ester CC(=O)O 4 971 867
24 O Carboxylic_ester CC(=O)O 4 971 867
25 C Primary_carbon, CH-acidic CC(=O)O 4 971 867
26 O Dialkylether, Heterocyclic, Epoxide O 5 971 867
0 C Primary_carbon CCNCC 1 937 868
1 C Primary_carbon CCNCC 1 937 868
8 C Secondary_carbon CCNCC 1 937 868
9 C Secondary_carbon CCNCC 1 937 868
10 N Secondary_aliph_amine, Heterocyclic CCNCC 1 937 868
11 O Alkylarylether CO 2 937 868
12 C Alkylarylether CO 2 937 868
13 O Alkylarylether CO 3 937 868
14 C Alkylarylether CO 3 937 868
17 C Alkylarylether C 1 927 869
21 O Alkylarylether CO 2 927 869
22 C Alkylarylether CO 2 927 869
23 O Alkylarylether CO 3 927 869
24 C Alkylarylether CO 3 927 869
0 C NA CCCN(C)C 1 887 870
1 N Tertiary_aliph_amine CCCN(C)C 1 887 870
2 C NA CCCN(C)C 1 887 870
3 C Secondary_carbon CCCN(C)C 1 887 870
4 C Secondary_carbon CCCN(C)C 1 887 870
5 C Secondary_carbon CCCN(C)C 1 887 870
16 C Aromatic cccc 2 887 870
17 C Aromatic cccc 2 887 870
18 C Aromatic cccc 2 887 870
19 C Aromatic cccc 2 887 870
0 C Aromatic cccc 1 896 871
1 C Aromatic cccc 1 896 871
2 C Aromatic cccc 1 896 871
5 C Aromatic, Conjugated_double_bond cccc 1 896 871
7 O Oxoarene, Conjugated_double_bond O 2 896 871
10 C Carboxylic_acid, Conjugated_double_bond O=CO 3 896 871
11 O Carboxylic_acid, Conjugated_double_bond O=CO 3 896 871
12 O Carboxylic_acid O=CO 3 896 871
0 C Alkylarylether CO 1 935 875
1 O Alkylarylether CO 1 935 875
16 O Phenol O 2 935 875
17 O Phenol O 3 935 875
12 O Phenol, 1,2-Diphenol O 1 894 881
13 O Phenol, 1,2-Diphenol O 2 894 881
14 O Secondary_alcohol, 1,2-Aminoalcohol O 3 894 881
0 C Primary_carbon C 1 897 893
2 C Primary_carbon C 2 897 893
8 C Aromatic, Conjugated_double_bond cccc 3 897 893
9 C Aromatic cccc 3 897 893
10 C Aromatic cccc 3 897 893
11 C Aromatic, Conjugated_double_bond cccc 3 897 893
14 O Ketone, Conjugated_double_bond O 4 897 893
16 O Ketone, Conjugated_double_bond O 5 897 893
2 O Ketone, Conjugated_double_bond O 1 969 894
9 O Alkylarylether CO 2 969 894
10 C Alkylarylether CO 2 969 894
12 C Alkylarylether C 3 969 894
13 O Phenol O 4 969 894
13 O Phenol O 1 1013 896
14 O Phenol O 2 1013 896
7 O Oxoarene, Conjugated_double_bond O 1 1009 897
0 C Primary_carbon CCC 1 984 903
1 C Primary_carbon, Alkene CCC 1 984 903
9 C Aromatic, Conjugated_double_bond ccc(=O)o 2 984 903
10 C Lactone, Aromatic, Conjugated_double_bond ccc(=O)o 2 984 903
11 C Lactone, Oxoarene, Aromatic, Conjugated_double_bond ccc(=O)o 2 984 903
12 O Lactone, Oxoarene, Conjugated_double_bond ccc(=O)o 2 984 903
13 O Lactone, Hetero_O, Heteroaromatic, Aromatic, Heterocyclic, Conjugated_double_bond ccc(=O)o 2 984 903
16 O Phenol O 3 984 903
17 C Primary_carbon CCC 1 984 903
0 C Alkylarylether CO 1 963 906
1 O Alkylarylether CO 1 963 906
4 C Aromatic cccc 2 963 906
5 C Aromatic cccc 2 963 906
6 C Aromatic cccc 2 963 906
7 C Aromatic cccc 2 963 906
12 C Aromatic cco 3 963 906
13 C Aromatic cco 3 963 906
14 O Hetero_O, Heteroaromatic, Aromatic, Heterocyclic cco 3 963 906
0 C Primary_carbon, Tertiary_carbon C 1 954 909
6 C Primary_carbon, Quaternary_carbon C 2 954 909
10 O Ketone O 3 954 909
12 C Primary_carbon, Tertiary_carbon C 4 954 909
17 O Alkylarylether CO 1 1025 910
18 C Alkylarylether CO 1 1025 910
5 C Primary_carbon C 1 934 911
8 C Carboxylic_acid, Conjugated_double_bond O=CO 2 934 911
9 O Carboxylic_acid, Conjugated_double_bond O=CO 2 934 911
10 O Carboxylic_acid O=CO 2 934 911
11 O Phenol O 3 934 911
17 C Primary_carbon C 4 934 911
21 C Primary_carbon C 5 934 911
24 C Alkylarylether C 6 934 911
25 O Alkylarylether CO 7 934 911
26 C Alkylarylether CO 7 934 911
0 C Primary_carbon, Secondary_carbon CCC 1 959 913
1 C Primary_carbon, Secondary_carbon CCC 1 959 913
2 C Secondary_carbon CCC 1 959 913
18 C Carboxylic_ester CC(O)CO 2 959 913
19 C Secondary_alcohol, 1,2-Diol CC(O)CO 2 959 913
20 C Primary_alcohol, 1,2-Diol CC(O)CO 2 959 913
21 O Primary_alcohol, 1,2-Diol CC(O)CO 2 959 913
22 O Secondary_alcohol, 1,2-Diol CC(O)CO 2 959 913
0 C Primary_carbon, CH-acidic CC(=O)O 1 1000 914
1 C Primary_carbon, Carboxylic_ester CC(=O)O 1 1000 914
2 O Carboxylic_ester CC(=O)O 1 1000 914
3 O Carboxylic_ester CC(=O)O 1 1000 914
6 O Phenol, 1,2-Diphenol O 1 933 919
8 O Phenol, 1,2-Diphenol O 2 933 919
32 O Ketone O 1 1010 920
24 O Ketone O 1 931 923
0 C Primary_carbon, Quaternary_carbon C 1 952 927
11 C Secondary_carbon, Tertiary_carbon CCC=O 2 952 927
12 C Secondary_carbon, Ketone, CH-acidic CCC=O 2 952 927
13 C Secondary_carbon, Quaternary_carbon, Ketone CCC=O 2 952 927
14 O Ketone CCC=O 2 952 927
16 C Primary_carbon, Quaternary_carbon C 3 952 927
2 O Ketone O 1 1017 928
11 C Alkene, Ketone, Conjugated_double_bond CCC(C)=O 2 1017 928
12 C Secondary_carbon, Ketone, Conjugated_double_bond CCC(C)=O 2 1017 928
13 O Ketone, Conjugated_double_bond CCC(C)=O 2 1017 928
14 C Secondary_carbon, Ketone, CH-acidic CCC(C)=O 2 1017 928
15 C Secondary_carbon, Quaternary_carbon CCC(C)=O 2 1017 928
23 O Carboxylic_ester CC(=O)O 3 1017 928
24 C Primary_carbon, Carboxylic_ester CC(=O)O 3 1017 928
25 O Carboxylic_ester CC(=O)O 3 1017 928
26 C Primary_carbon, CH-acidic CC(=O)O 3 1017 928
0 C Alkylarylether CO 1 987 929
1 O Alkylarylether CO 1 987 929
19 O Phenol O 2 987 929
28 O Ketone O 1 983 930
6 O Aldehyde, Conjugated_double_bond O 1 939 934
24 C Carboxylic_ester C 2 939 934
0 C Alkene C=CC(C)(C)O 1 949 935
1 C Alkene C=CC(C)(C)O 1 949 935
2 C Primary_carbon, Secondary_carbon, Tertiary_alcohol C=CC(C)(C)O 1 949 935
3 C Primary_carbon C=CC(C)(C)O 1 949 935
4 C Secondary_carbon C=CC(C)(C)O 1 949 935
8 C Alkene C 2 949 935
12 C Primary_carbon, Secondary_carbon, Tertiary_carbon, Quaternary_carbon CCCC(C)C 3 949 935
13 C Primary_carbon, Quaternary_carbon CCCC(C)C 3 949 935
14 C Primary_carbon, Quaternary_carbon CCCC(C)C 3 949 935
15 C Secondary_carbon, Quaternary_carbon CCCC(C)C 3 949 935
16 C Secondary_carbon CCCC(C)C 3 949 935
17 C Secondary_carbon, Quaternary_carbon CCCC(C)C 3 949 935
19 C Primary_carbon, Quaternary_carbon C 4 949 935
21 O Tertiary_alcohol C=CC(C)(C)O 1 949 935
7 O Carboxylic_acid, Conjugated_double_bond O 1 1013 937
8 O Carboxylic_acid O 2 1013 937
13 O Phenol O 3 1013 937
14 O Phenol O 4 1013 937
6 O Ketone O 1 965 940
32 O Secondary_alcohol O 2 965 940
8 C Carboxylic_ester C 1 985 941
2 C Secondary_carbon, Quaternary_carbon CCC(C)O 1 952 943
3 C Secondary_carbon CCC(C)O 1 952 943
4 C Secondary_carbon, Secondary_alcohol CCC(C)O 1 952 943
5 C Secondary_carbon, Tertiary_carbon CCC(C)O 1 952 943
11 C Secondary_carbon, Tertiary_carbon CCC=O 2 952 943
12 C Secondary_carbon, Ketone, CH-acidic CCC=O 2 952 943
13 C Secondary_carbon, Quaternary_carbon, Ketone CCC=O 2 952 943
14 O Ketone CCC=O 2 952 943
20 O Secondary_alcohol CCC(C)O 1 952 943
24 O Ketone O 1 1011 945
0 C Primary_carbon, Tertiary_carbon CCCO 1 1012 948
1 C Primary_carbon, Tertiary_carbon CCCO 1 1012 948
2 C Tertiary_carbon, Enolether CCCO 1 1012 948
3 O Enolether, Heterocyclic CCCO 1 1012 948
9 O Ketone, Conjugated_double_bond O 2 1012 948
16 C Primary_carbon, Quaternary_carbon C 3 1012 948
17 C Primary_carbon, Quaternary_carbon C 4 1012 948
8 O Carboxylic_acid, Conjugated_double_bond O 1 950 949
9 O Carboxylic_acid O 2 950 949
10 O Phenol O 3 950 949
0 C Primary_carbon, Ketone, CH-acidic C 1 969 950
10 C Alkylarylether C 2 969 950
12 C Alkylarylether C 3 969 950
13 O Phenol O 4 969 950
0 C Alkylarylether CO 1 987 951
1 O Alkylarylether CO 1 987 951
18 O Oxoarene, Conjugated_double_bond O 2 987 951
19 O Phenol O 3 987 951
0 C Alkene, Conjugated_double_bond C=CC=O 1 957 952
1 C Tertiary_carbon, Alkene, Ketone, Conjugated_double_bond C=CC=O 1 957 952
7 C Quaternary_carbon, Hemiacetal CO 2 957 952
8 O Hemiacetal, Acetal_like, Heterocyclic, Sugar_pattern_2, Sugar_pattern_2_reducing CO 2 957 952
14 C Primary_carbon, Quaternary_carbon C 3 957 952
18 O Secondary_alcohol O 4 957 952
19 O Secondary_alcohol O 5 957 952
21 C Quaternary_carbon, Ketone, Conjugated_double_bond C=CC=O 1 957 952
22 O Ketone, Conjugated_double_bond C=CC=O 1 957 952
24 O Secondary_alcohol O 6 957 952
0 C Primary_carbon, Tertiary_carbon CCC(=O)O 1 954 953
1 C Primary_carbon, Tertiary_carbon, Lactone, CH-acidic CCC(=O)O 1 954 953
6 C Primary_carbon, Quaternary_carbon C 2 954 953
7 C Secondary_carbon, Quaternary_carbon CCC(=O)CC 3 954 953
8 C Secondary_carbon, Ketone, CH-acidic CCC(=O)CC 3 954 953
9 C Secondary_carbon, Tertiary_carbon, Ketone CCC(=O)CC 3 954 953
10 O Ketone CCC(=O)CC 3 954 953
11 C Primary_carbon, Tertiary_carbon, Ketone, CH-acidic CCC(=O)CC 3 954 953
12 C Primary_carbon, Tertiary_carbon CCC(=O)CC 3 954 953
15 O Lactone, Heterocyclic CCC(=O)O 1 954 953
16 C Tertiary_carbon, Lactone CCC(=O)O 1 954 953
17 O Lactone CCC(=O)O 1 954 953
2 C Quaternary_carbon, Alkene, Conjugated_double_bond C=CC(C)=O 1 975 954
3 C Alkene, Ketone, Conjugated_double_bond C=CC(C)=O 1 975 954
4 C Ketone, Conjugated_double_bond C=CC(C)=O 1 975 954
5 O Ketone, Conjugated_double_bond C=CC(C)=O 1 975 954
6 C Alkene, Ketone, Conjugated_double_bond C=CC(C)=O 1 975 954
12 C Secondary_carbon, Tertiary_carbon CCC=O 2 975 954
13 C Secondary_carbon, Ketone, CH-acidic CCC=O 2 975 954
14 C Secondary_carbon, Quaternary_carbon, Ketone CCC=O 2 975 954
15 O Ketone CCC=O 2 975 954
7 O Oxoarene, Conjugated_double_bond O 1 1009 955
9 C Aromatic, Conjugated_double_bond cccc 2 1009 955
10 C Aromatic cccc 2 1009 955
11 C Aromatic cccc 2 1009 955
12 C Aromatic cccc 2 1009 955
7 O Ketone, Conjugated_double_bond O 1 961 957
15 O Ketone, Conjugated_double_bond O 2 961 957
6 O Phenol O 1 1015 958
7 O Phenol O 2 1015 958
12 O Primary_alcohol O 1 972 959
13 O Secondary_alcohol, 1,2-Diol O 2 972 959
14 O Secondary_alcohol, 1,2-Diol O 3 972 959
0 C Primary_carbon, Ketone, CH-acidic CCCC(C)=O 1 1017 961
1 C Primary_carbon, Tertiary_carbon, Ketone CCCC(C)=O 1 1017 961
2 O Ketone CCCC(C)=O 1 1017 961
3 C Secondary_carbon, Tertiary_carbon, Quaternary_carbon, Ketone, CH-acidic CCCC(C)=O 1 1017 961
4 C Secondary_carbon, Tertiary_carbon CCCC(C)=O 1 1017 961
5 C Secondary_carbon, Tertiary_carbon CCCC(C)=O 1 1017 961
11 C Alkene, Ketone, Conjugated_double_bond CCC(C)=O 2 1017 961
12 C Secondary_carbon, Ketone, Conjugated_double_bond CCC(C)=O 2 1017 961
13 O Ketone, Conjugated_double_bond CCC(C)=O 2 1017 961
14 C Secondary_carbon, Ketone, CH-acidic CCC(C)=O 2 1017 961
15 C Secondary_carbon, Quaternary_carbon CCC(C)=O 2 1017 961
17 C Primary_carbon, Quaternary_carbon C 3 1017 961
22 C Primary_carbon, Quaternary_carbon C 4 1017 961
24 C Primary_carbon, Carboxylic_ester CC=O 5 1017 961
25 O Carboxylic_ester CC=O 5 1017 961
26 C Primary_carbon, CH-acidic CC=O 5 1017 961
0 C Alkylarylether C 1 987 962
19 O Phenol O 2 987 962
6 C Carboxylic_acid, Conjugated_double_bond O=CO 1 1013 963
7 O Carboxylic_acid, Conjugated_double_bond O=CO 1 1013 963
8 O Carboxylic_acid O=CO 1 1013 963
13 O Phenol O 2 1013 963
7 Cl Arylchloride Cl 1 1002 964
9 Cl Arylchloride Cl 2 1002 964
17 C Primary_carbon C 3 1002 964
26 C Carboxylic_ester C 4 1002 964
30 O Ketone O 1 1021 965
31 O Dialkylether, Heterocyclic, Epoxide O 2 1021 965
32 O Secondary_alcohol O 3 1021 965
0 C NA CN 1 1008 969
1 N Secondary_aliph_amine CN 1 1008 969
0 C Primary_carbon, Ketone, CH-acidic C 1 1017 971
2 O Ketone O 2 1017 971
13 O Ketone, Conjugated_double_bond O 3 1017 971
17 C Primary_carbon, Quaternary_carbon C 4 1017 971
22 C Primary_carbon, Quaternary_carbon C 5 1017 971
23 O Carboxylic_ester CC(=O)O 6 1017 971
24 C Primary_carbon, Carboxylic_ester CC(=O)O 6 1017 971
25 O Carboxylic_ester CC(=O)O 6 1017 971
26 C Primary_carbon, CH-acidic CC(=O)O 6 1017 971
0 C Alkylarylether CO 1 1014 974
1 O Alkylarylether CO 1 1014 974
8 O Phenol O 2 1014 974
12 O Carboxylic_acid, Conjugated_double_bond O 3 1014 974
13 O Carboxylic_acid O 4 1014 974
0 C Primary_carbon, Ketone, CH-acidic CC=O 1 1017 975
1 C Primary_carbon, Tertiary_carbon, Ketone CC=O 1 1017 975
2 O Ketone CC=O 1 1017 975
11 C Alkene, Ketone, Conjugated_double_bond CCC(C)=O 2 1017 975
12 C Secondary_carbon, Ketone, Conjugated_double_bond CCC(C)=O 2 1017 975
13 O Ketone, Conjugated_double_bond CCC(C)=O 2 1017 975
14 C Secondary_carbon, Ketone, CH-acidic CCC(C)=O 2 1017 975
15 C Secondary_carbon, Quaternary_carbon CCC(C)=O 2 1017 975
23 O Carboxylic_ester CC(=O)O 3 1017 975
24 C Primary_carbon, Carboxylic_ester CC(=O)O 3 1017 975
25 O Carboxylic_ester CC(=O)O 3 1017 975
26 C Primary_carbon, CH-acidic CC(=O)O 3 1017 975
8 O Alkylarylether CO 1 978 977
9 C Alkylarylether CO 1 978 977
27 O Alkylarylether CO 1 979 978
28 C Alkylarylether CO 1 979 978
6 C Carboxylic_acid, Conjugated_double_bond O=CO 1 1013 980
7 O Carboxylic_acid, Conjugated_double_bond O=CO 1 1013 980
8 O Carboxylic_acid O=CO 1 1013 980
13 O Phenol O 2 1013 980
14 O Phenol O 3 1013 980
31 O Dialkylether, Heterocyclic, Epoxide O 1 1021 981
30 O Ketone O 1 1021 983
31 O Dialkylether, Heterocyclic, Epoxide O 2 1021 983
32 O Secondary_alcohol O 3 1021 983
0 C Primary_carbon CC=C(C)C 1 990 984
1 C Primary_carbon, Alkene CC=C(C)C 1 990 984
2 C Secondary_carbon, Alkene CC=C(C)C 1 990 984
3 C Secondary_carbon CC=C(C)C 1 990 984
10 O Oxoarene, Conjugated_double_bond O 2 990 984
13 C Primary_carbon C 3 990 984
16 O Phenol O 4 990 984
18 C Primary_carbon CC=C(C)C 1 990 984
17 O Phenol O 1 989 986
20 O Phenol, 1,2-Diphenol O 1 1006 987
21 O Phenol, 1,2-Diphenol O 2 1006 987
6 O Phenol O 1 1015 989
7 O Phenol O 2 1015 989
19 O Phenol O 3 1015 989
21 O Phenol O 4 1015 989
0 C Primary_carbon CC=C(C)C 1 991 990
1 C Primary_carbon, Alkene CC=C(C)C 1 991 990
2 C Secondary_carbon, Alkene CC=C(C)C 1 991 990
3 C Secondary_carbon CC=C(C)C 1 991 990
18 C Alkylarylether C 2 991 990
19 C Primary_carbon CC=C(C)C 1 991 990
9 C Aromatic, Conjugated_double_bond cccc 1 1009 991
10 C Aromatic cccc 1 1009 991
11 C Aromatic cccc 1 1009 991
12 C Aromatic cccc 1 1009 991
0 C NA C=[N+](C)CC 1 995 993
1 N Immonium, Heterocyclic, Conjugated_double_bond, Kation C=[N+](C)CC 1 995 993
2 C Conjugated_double_bond C=[N+](C)CC 1 995 993
5 C Secondary_carbon C=[N+](C)CC 1 995 993
6 C Secondary_carbon C=[N+](C)CC 1 995 993
12 C Alkylarylether C 2 995 993
13 O Acetal, Acetal_like, Heterocyclic OCO 3 995 993
14 C Acetal, Acetal_like OCO 3 995 993
15 O Acetal, Acetal_like, Heterocyclic OCO 3 995 993
8 O Alkylarylether CO 1 1004 995
9 C Alkylarylether CO 1 1004 995
10 O Alkylarylether CO 2 1004 995
11 C Alkylarylether CO 2 1004 995
12 O Phenol O 3 1004 995
0 C Alkylarylether CO 1 1004 996
1 O Alkylarylether CO 1 1004 996
8 O Alkylarylether CO 2 1004 996
9 C Alkylarylether CO 2 1004 996
10 O Alkylarylether CO 3 1004 996
11 C Alkylarylether CO 3 1004 996
12 O Phenol O 4 1004 996
0 C Primary_carbon, Tertiary_carbon C 1 1012 1001
7 O Ketone, Conjugated_double_bond O 2 1012 1001
9 O Ketone, Conjugated_double_bond O 3 1012 1001
16 C Primary_carbon, Quaternary_carbon C 4 1012 1001
17 C Primary_carbon, Quaternary_carbon C 5 1012 1001
0 C NA CNC 1 1008 1004
1 N Secondary_aliph_amine CNC 1 1008 1004
2 C NA CNC 1 1008 1004
0 C Alkylarylether C 1 1022 1006
10 O Phenol O 2 1022 1006
22 O Phenol O 3 1022 1006
23 O Alkylarylether CO 4 1022 1006
24 C Alkylarylether CO 4 1022 1006
0 C Alkylarylether CO 1 1014 1008
1 O Alkylarylether CO 1 1014 1008
8 O Phenol O 2 1014 1008
10 C Alkene, Conjugated_double_bond CC(=O)O 3 1014 1008
11 C Carboxylic_acid, Conjugated_double_bond CC(=O)O 3 1014 1008
12 O Carboxylic_acid, Conjugated_double_bond CC(=O)O 3 1014 1008
13 O Carboxylic_acid CC(=O)O 3 1014 1008
38 C Carboxylic_ester C 1 1020 1010
45 C Alkylarylether C 2 1020 1010
0 C Primary_carbon, Ketone, CH-acidic CCCC(C)=O 1 1017 1012
1 C Primary_carbon, Tertiary_carbon, Ketone CCCC(C)=O 1 1017 1012
2 O Ketone CCCC(C)=O 1 1017 1012
3 C Secondary_carbon, Tertiary_carbon, Quaternary_carbon, Ketone, CH-acidic CCCC(C)=O 1 1017 1012
4 C Secondary_carbon, Tertiary_carbon CCCC(C)=O 1 1017 1012
5 C Secondary_carbon, Tertiary_carbon CCCC(C)=O 1 1017 1012
17 C Primary_carbon, Quaternary_carbon C 2 1017 1012
23 O Carboxylic_ester CC(=O)O 3 1017 1012
24 C Primary_carbon, Carboxylic_ester CC(=O)O 3 1017 1012
25 O Carboxylic_ester CC(=O)O 3 1017 1012
26 C Primary_carbon, CH-acidic CC(=O)O 3 1017 1012
0 C Alkylarylether C 1 1019 1015
8 O Alkylarylether CO 2 1019 1015
9 C Alkylarylether CO 2 1019 1015
21 O Alkylarylether CO 3 1019 1015
22 C Alkylarylether CO 3 1019 1015
24 C Alkylarylether C 4 1019 1015
25 O Alkylarylether CO 5 1019 1015
26 C Alkylarylether CO 5 1019 1015
28 C Alkylarylether C 6 1019 1015
Code 
remove_smiles <- comparison_table_remove %>%
  group_by(idx1) %>%
  distinct(frag_smiles)
add_smiles <- comparison_table_add %>%
  group_by(idx1) %>%
  distinct(frag_smiles)

combined_factors <- factor(c(remove_smiles$frag_smiles, add_smiles$frag_smiles))
counts <- tabulate(combined_factors)
names <- levels(combined_factors)
result <- data.frame(
  Frag_SMILES = names,
  Count = counts
)

# Print the result
result %>% kable()
Frag_SMILES Count
[N-]=[N+]=N 1
[nH]c([nH])=O 1
[nH]c(=O)[nH]c=O 1
[nH]c(=O)c([nH])=O 1
[nH]c(=O)o 1
[nH]ccCCN 1
[nH]cn 1
[nH]n 2
[OH-] 1
Br 14
C 315
C#C 3
C#CC 2
C#CCO 1
C#N 8
CN+[O-] 1
CN+(C)C 2
CN+C 1
C[N+]C 1
c[nH] 1
c[nH]n 2
CSH=O 3
C=N+CC 2
C=C 4
C=C(C)C 3
C=CC 5
C=CC#N 1
C=CC(=O)O 1
C=CC(C)(C)O 5
C=CC(C)=O 2
C=CC=O 2
C=CCO 2
C1=CCC=CC1 1
C1=CCCC1 1
C1=NCCCS1 2
C1=NCCN1 6
c1c[nH]cn1 3
C1CC1 7
C1CCCC1 7
c1ccccc1 44
C1CCCCC1 5
C1CCNC1 3
c1ccncc1 11
C1CCNCC1 4
c1ccoc1 4
C1CCOCC1 1
C1CN1 1
C1CNC1 2
C1CNCCN1 3
c1cncn1 3
c1cncnc1 1
c1cnnc1 1
C1COC1 1
C1COCCN1 4
C1COCO1 2
c1cscn1 2
C1CSCS1 1
c1csnn1 1
c1ncnn1 8
CBr 1
CC 48
CC(=O)O 21
CC(=O)S 1
CC(C)(C)O 1
CC(C)=CCN 1
CC(C)=NN 1
CC(C)=O 1
CC(C)C 16
CC(C)C=O 1
CC(C)CCN 1
CC(C)N 4
CC(C)NN 1
CC(C)O 4
CC(C)OC=O 1
cc(Cl)c(c)Cl 2
cc(Cl)cn 1
CC(N)=O 2
CC(N)C(=O)O 1
cc(O)c(c)O 1
Cc(o)cc=O 1
CC(O)CO 2
CCN+(C)C 1
cc[nH] 5
CC=C(C)C 8
CC=C(C)CO 1
CC=CCO 1
CC=O 15
CC1C=CCC1 1
Cc1ccco1 1
Cc1cccs1 1
Cc1ccno1 1
CC1CCOC1 1
Cc1ccsn1 1
ccc 4
CCC 41
ccc([nH])=O 1
CCC(=O)CC 1
ccc(=O)o 3
CCC(=O)O 5
CCC(=O)OC 2
CCC(C)(C)C 1
CCC(C)(C)O 2
CCC(C)=O 1
ccc(c)C#N 1
ccc(c)Cl 1
ccc(c)F 1
ccc(c)I 1
CCC(C)NC 1
ccc(c)O 1
CCC(C)O 2
ccc(n)Cl 1
ccc(O)cO 1
CCC=[NH+][O-] 2
CCC=O 4
cccc 27
CCCC 9
CCCC(C)=O 1
CCCC(C)C 2
CCCC(O)O 1
ccccc 2
CCCCC 4
ccccCl 1
CCCCN 5
ccccO 1
CCCCO 2
CCCl 1
cccn 2
CCCN 3
CCCN(C)C 4
CCCNCC 1
CCCO 6
CCCOC 1
CCCOC=O 2
CCCS 4
CCl 1
CCN 9
CCN(C)C 7
CCN(C)CC 2
CCN=C(N)S 1
ccnc 3
ccnC 1
CCNC 7
CCnc([nH])=O 2
ccncC 1
CCNCC 6
cco 5
CCO 13
CCOC 2
CCOC(N)=O 1
CCOC=O 1
CCON 1
ccs 1
CCS 4
CCS(N)(=O)=O 2
CCSC(C)C 1
CCSC=O 2
Cl 132
Cl[Hg] 2
CN 24
CN(C)SH=O 2
CN(C)C 2
CN(C)C(N)=O 1
CN(C)C=O 3
CN(C)CCO 2
cn[nH] 3
CN=C(N)N 1
CN1CCCC1 1
Cn1ccsc1 1
Cn1cncn1 4
CNC 16
CNC(=O)CS 2
CNC(=O)O 4
CNC(=O)ON 2
CNC(C)C 3
cnc(n)N 2
CNC=O 3
CNCC(C)C 1
CNCCN 1
cnn 1
cnnCC 1
cnncNN 1
cno 1
CNS(C)(=O)=O 1
CO 100
COPHOC 2
COPH=S 1
COC 1
COC(C)=O 1
COC(N)=O 1
COC=O 8
CON 3
COP(=O)(O)O 1
CS 11
CS(N)(=O)=O 2
CSC 2
CSN=O 1
F 18
FC(F)C(F)F 1
FC(F)F 12
FC(S)(Cl)Cl 1
I 12
N 67
N#CN 2
NN+[O-] 1
NSH=O 7
N=C(N)N 1
N=CN 3
nc(N)[nH]c=O 1
NC(N)=NC=O 2
nc(N)ncN 1
nc(N)s 2
nc[nH] 1
NC=NSH=O 1
NC=O 6
NC=S 3
NC1=NCCN1 1
Nc1nccs1 2
NCC(=O)O 3
NCCON 1
NCN 1
NCNN+[O-] 1
NCNSH=O 2
ncncN 2
NN 1
nnn 1
nnnN 1
NO[SH]=O 1
NS(=O)O 2
O 353
O=[NH+][O-] 17
O=SHF 1
O=SHO 1
O=C(O)C1CO1 1
O=C1CCCN1 3
O=C1NCCS1 1
O=CCCl 3
O=CCO 2
O=CO 41
O=NS 2
OC(=S)S 1
OC(F)(F)F 2
OC1CCCC1 2
OC1COC1 1
OCC(Cl)(Cl)Cl 1
OCC(O)CO 1
OccccF 1
OCCCl 1
OCCO 2
OCO 7
S 10
S=CS 1

Functional groups (common)

Code 
fg_df_common1 <- analyze_smiles_vector(comparison_table$common1)
fg_df_common1<-fg_df_common1%>%mutate(id1 = comparison_table$id1,
                      id2 = comparison_table$id2, .before = SMILES)
write.csv(fg_df_common1, file = here(data_deliv_dir,"smarts_functional_groups_common1.csv"), row.names = FALSE)


fg_df_common2 <- analyze_smiles_vector(comparison_table$common2)
fg_df_common2<-fg_df_common2%>%mutate(id1 = comparison_table$id1,
                      id2 = comparison_table$id2, .before = SMILES)
write.csv(fg_df_common2, file = here(data_deliv_dir,"smarts_functional_groups_common2.csv"), row.names = FALSE)
Code 
foo_remove<- fg_df[comparison_table$id1,4:273]-fg_df_common1[,4:273]
foo_add<- fg_df[comparison_table$id2,4:273]-fg_df_common2[,4:273]
foo <- foo_add-foo_remove

foo<-foo %>%mutate(id1 = comparison_table$id1,
                      id2 = comparison_table$id2, .before = colnames(foo)[1])
Code 
set.seed(123)
idx=sample(1:637,12)
idx1 = results_selected_crit$mol1_index[idx]
idx2 = results_selected_crit$mol2_index[idx]
idx = which(comparison_table$id1%in%idx1 & comparison_table$id2%in%idx2)

foo[idx,]%>%select(where(~ !all(. == 0)))
      id1 id2 Primary_carbon Secondary_carbon Tertiary_carbon Quaternary_carbon
669.1 411 669             -1               -2               0                 0
95.1   14  95              2                0               1                 0
273   215 273              1                0               0                 0
409   126 409              1               -1              -1                 0
862   535 862              0                0               0                 0
952.2 676 952             -1                1              -1                 0
961.1 957 961             -2               -4              -3                -3
510.1 326 510              0                0               0                 0
256   245 256              0                0               0                 0
722.1 304 722              4                0               1                 1
662   598 662              0                0               0                 0
885.2 799 885              0               -1              -3                 0
      Alkene Alkylchloride Primary_alcohol Secondary_alcohol Alkylarylether
669.1      0             0               0                 0              0
95.1       0             0              -2                -3              0
273        0             0               0                 1              0
409        0             1               0                 1              0
862        0             0               0                 0              1
952.2      0             0               0                 0              0
961.1     -1             0               0                -3              0
510.1      0             0               0                 0              0
256        0             1               0                 0              1
722.1      0             0               0                 0              0
662        0             0               0                 0              1
885.2      0             0               0                -1              0
      Diarylthioether Oxonium Primary_aliph_amine Tertiary_aliph_amine
669.1               0       0                   0                    0
95.1                0       0                   1                    0
273                 0       0                   0                    0
409                 0       0                   0                    0
862                 0       0                   0                    0
952.2               0       0                   0                    0
961.1               0       0                   0                    0
510.1               0       0                   0                    0
256                 1       1                   0                   -1
722.1               0       0                   0                    0
662                 0       0                   0                    0
885.2               0       0                   0                    0
      Tertiary_arom_amine Secondary_mixed_amine X1.2.Diol Ketone Hemiacetal
669.1                   0                    -1         0      0          0
95.1                    0                     0        -4      0          0
273                     1                     0         0     -1          0
409                     0                     0         0     -1          0
862                     0                     0         0      0          0
952.2                   0                     0         0     -1          0
961.1                   0                     0         0      1         -1
510.1                   0                     0         0      0          0
256                     0                     0         0      0          0
722.1                   0                     0         0      0          0
662                     0                     0         0      0          0
885.2                   0                     0         0      0          0
      Acetal_like Carboxylic_acid Carboxylic_ester Imidoylhalide_cyclic
669.1           0              -1                0                    0
95.1            0               1                0                    0
273             0               0                0                    0
409             0               0                0                    0
862             0               0                0                    0
952.2           0               0                0                    0
961.1          -1               0                0                    0
510.1           0               0                0                    0
256             0               0               -1                    0
722.1           0               0                0                   -1
662             0               0                0                    0
885.2           0               0               -1                    0
      Alpha_aminoacid Nitrile Urea Guanidine Phenol X1.2.Diphenol Arylchloride
669.1               0       0    0         0      0             0            0
95.1                1       0    0         0      0             0            0
273                 0       0    0         0      0             0            0
409                 0       0    0         0      0             0            0
862                 0       0    0         0     -2            -1            0
952.2               0       0    0         0      0             0            0
961.1               0       0    0         0      3             1            0
510.1               0       0   -1         2      0             0           -1
256                 0       0    0         0      0             0            0
722.1               0       1   -1         1      0             0           -1
662                 0       0    0         0      0             0            0
885.2               0       0    0         0      0             0            0
      Oxoarene Hetero_N_basic_H Hetero_O Nitro Borohydride Aromatic
669.1        0                0        0     1           0        0
95.1         0                0        0     0           0        0
273         -1                0       -1     0          -3        0
409          0                0        0     0           0        0
862          0                0        0     0           0        0
952.2        0                0        0     0           0        0
961.1        0                0        0     0           0       12
510.1        0                0        0     0           0        0
256          0               -1       -1     0          -6        0
722.1        0                0        0     0           0       -6
662          0                0        0     0           0        0
885.2        0                0        0     0           0        6
      Heterocyclic NH_aziridine Spiro Annelated_rings Bridged_rings
669.1            0            0     0               0             0
95.1             0            0     0               0             0
273              0            0     0               0             0
409              0            0     0               0             0
862              0            0     0               0             0
952.2            0            0     0               0             0
961.1           -1            0    -2              -2            -1
510.1            0            0     0               0             0
256              0            0     0               0             0
722.1            0           -1     0               0             0
662              0            0     0               0             0
885.2            0            0     0              -2             0
      Sugar_pattern_2 Sugar_pattern_2_reducing Conjugated_double_bond
669.1               0                        0                     -4
95.1                0                        0                      0
273                 0                        0                      0
409                 0                        0                      0
862                 0                        0                      0
952.2               0                        0                      0
961.1              -1                       -1                      7
510.1               0                        0                      0
256                 0                        0                     -2
722.1               1                        0                      1
662                 0                        0                      0
885.2               0                        0                      0
      Conjugated_tripple_bond Anion Kation CH.acidic
669.1                       0     1      1         0
95.1                        0     0      0         0
273                         0     0      0         0
409                         0     0      0        -2
862                         0     0      0         0
952.2                       0     0      0        -3
961.1                       0     0      0         0
510.1                       0     0      0         0
256                         0     0      0         0
722.1                       1     0     -1         0
662                         0     0      0         0
885.2                       0     0      0        -1
Code 
comparison_table[idx,] %>%
  select("id1", "id2", "structure") %>%
  kbl(escape = FALSE, format = "html", align = "l") %>%
  kable_styling(full_width = FALSE, position = "center", bootstrap_options = c("striped", "hover", "condensed"))
id1 id2 structure
395 411 669
510 14 95
559 215 273
632 126 409
653 535 862
676 676 952
697 957 961
748 326 510
830 245 256
855 304 722
967 598 662
995 799 885
Code 
listx = comparison_table[idx,]
map(1:min(20, nrow(listx)), \(x) plotting_i(x, listx)) %>% wrap_plots(ncol = 4)

Session info

Code 
sessionInfo()
R version 4.3.1 (2023-06-16 ucrt)
Platform: x86_64-w64-mingw32/x64 (64-bit)
Running under: Windows 10 x64 (build 19045)

Matrix products: default


locale:
[1] LC_COLLATE=Polish_Poland.utf8  LC_CTYPE=Polish_Poland.utf8   
[3] LC_MONETARY=Polish_Poland.utf8 LC_NUMERIC=C                  
[5] LC_TIME=Polish_Poland.utf8    

time zone: Europe/Warsaw
tzcode source: internal

attached base packages:
[1] stats     graphics  grDevices utils     datasets  methods   base     

other attached packages:
 [1] lubridate_1.9.3   forcats_1.0.0     stringr_1.5.1     purrr_1.0.2      
 [5] readr_2.1.5       tibble_3.2.1      tidyverse_2.0.0   ggraph_2.2.1     
 [9] igraph_2.1.4      visNetwork_2.1.2  kableExtra_1.4.0  reticulate_1.42.0
[13] magick_2.8.6      here_1.0.1        pracma_2.4.4      reshape2_1.4.4   
[17] GGally_2.2.1      dplyr_1.1.4       tidyr_1.3.1       patchwork_1.2.0  
[21] gridExtra_2.3     ggplot2_3.5.1    

loaded via a namespace (and not attached):
 [1] gtable_0.3.5       xfun_0.44          htmlwidgets_1.6.4  ggrepel_0.9.6     
 [5] lattice_0.21-8     tzdb_0.4.0         vctrs_0.6.5        tools_4.3.1       
 [9] generics_0.1.3     fansi_1.0.6        pkgconfig_2.0.3    Matrix_1.6-5      
[13] RColorBrewer_1.1-3 lifecycle_1.0.4    compiler_4.3.1     farver_2.1.2      
[17] textshaping_0.4.0  munsell_0.5.1      ggforce_0.4.2      graphlayouts_1.2.2
[21] htmltools_0.5.8.1  yaml_2.3.8         pillar_1.9.0       MASS_7.3-60       
[25] cachem_1.1.0       viridis_0.6.5      ggstats_0.8.0      tidyselect_1.2.1  
[29] digest_0.6.35      stringi_1.8.4      labeling_0.4.3     polyclip_1.10-7   
[33] rprojroot_2.0.4    fastmap_1.2.0      grid_4.3.1         colorspace_2.1-0  
[37] cli_3.6.2          magrittr_2.0.3     tidygraph_1.3.1    utf8_1.2.4        
[41] withr_3.0.2        scales_1.3.0       timechange_0.3.0   rmarkdown_2.27    
[45] hms_1.1.3          ragg_1.3.2         png_0.1-8          memoise_2.0.1     
[49] evaluate_1.0.3     knitr_1.46         viridisLite_0.4.2  rlang_1.1.3       
[53] Rcpp_1.0.12        glue_1.7.0         tweenr_2.0.3       xml2_1.3.6        
[57] svglite_2.1.3      rstudioapi_0.16.0  jsonlite_1.8.8     R6_2.5.1          
[61] plyr_1.8.9         systemfonts_1.1.0